Chuck and Blair
First and foremost, Blair and Chuck were always and have always been the complicated couple - the couple that tricks and manipulates each other at times, but in actual reality this is due to their mutual struggle to openly display their love for each other. Despite the couple's prominent traits being outwardly deceptive, fans and viewers of Gossip Girl often believe that "Chair" truly cherish and love each other so deeply, arguably cementing their status as the show's inevitable and central relationship.
Chuck and Blair grew up on the Upper East Side, both members of elite families. They, and their respective best friends Nate Archibald and Serena van der Woodsen, have known each other since birth and attended school together. At the beginning of Season One, it is shown that Blair has a mild disdain for Chuck and he has an indifference toward her. However, the pair are friends and often partner up to scheme against others to keep their positions at the top.
The first hint of a mutually romantic bond is in Victor, Victrola, where the two meet up and Blair loses her virginity to Chuck in the back of his limo. This is considered a regretted one-night stand on Blair's part, as she had broken up with her boyfriend, Nate, just before she left for the club. However, their sexual relationship resumes after a short period of time, though they keep it secret. The pair intend to go away together during the summer, but Chuck breaks Blair's heart at the end of the season by changing his mind.
In Pilot, Chuck and Blair appear to have an acquaintance-like friendship. We first see them interact at Blair's mother's party, where Blair hints to Chuck that she intends for her and Nate to have sex. Throughout the episode, Chuck talks openly to Nate about how he should 'seal the deal' with Blair. It is obvious that at this point in time, neither Blair nor Chuck have any romantic feelings toward each other. At the end of the episode, the two share a comrade-like moment which is one of the first times that they speak to each other in the series.
In The Wild Brunch, Blair and Chuck sit together, along with Nate, Isabel Coates and Kati Farkas, at Chuck's father Bart's brunch. They appear to be having a friendly, good time before Serena and Dan arrive. The two showing up at the brunch angers Chuck and Blair, due to the fact that Serena slept with Nate and the fact that Dan punched Chuck at the Kiss on the Lips Party. Blair talks about her anger to Chuck, who brings up her worry for her boyfriend. He then offers to help by giving her the key to his suite. They both take part in informing Dan about Serena's indiscretions with Nate.
In Poison Ivy, the junior class is trying to get into the Ivy League schools, and this includes Chuck and Blair. Chuck calls Blair after a fight between Blair and Serena. He starts the conversation with sexual comments, and she states her distaste for them. However, the call swiftly turns into one with a purpose, which is Blair wanting dirt on Serena and Chuck being happy to comply. This is the first 'scheme' of sorts that the two team up for in the show. Chuck soon does as promised, and calls Blair immediately to tell her that he found something out. She covers up the identity of the caller from Nate by pretending it's her mother, Eleanor. In her bedroom later, Chuck shows her the pictures of Serena at the Ostroff Center, and she gives a positive response. He makes a suggestive comment about Blair's bed, and she abruptly tells him to leave. Later, Blair approaches Chuck, scolding him for allowing Serena to take over being the Yale representative's usher. He then walks in as she and Eric are speaking about his time at the Center.Victor, Victrola is the real turning point in the relationship between Chuck and Blair. The episode starts with a burlesque scene, which turns into a scene with Chuck watching a woman (who is later revealed to be Blair) dance on the stage. The scene then changes to two days earlier. Chuck is excitedly telling Blair about the burlesque club that
That night during a dinner with their families, Blair and Nate get into a fight about Nate's father, and Blair asks Nate whether he loves her. Nate doesn't say anything, so Blair tells him to deal with his father, since he needs him, and she doesn't. Blair gets into the limo and goes to Victrola for Chuck´s party.When she gets out of the limo, Blair tells Chuck that she thinks that she and Nate broke up, before walking inside and stating her want to escape. While sitting in the club and drinking, Chuck shows his care by trying to ask about the break up and how she felt. Blair says she feels relieved. While watching the women dance on the stage, she tells Chuck that she has moves. After Chuck half dares her to prove it, she goes onto the stage and dances, stripping to her slip. Chuck watches, enticed and dumbfounded, stating to somebody who asked that he didn't know who Blair was. Later, the two are in Chuck's limo and Blair thanks him for taking her home. He says that she was amazing on the stage, and she moves closer to kiss him. He asks if she is sure, knowing that she can be vulnerable after the break up. She starts kissing Chuck passionately. Blair gives her virginity to Chuck in the back of his limo.
In Seventeen Candles, it is Blair's seventeenth birthday. The episode starts with Blair confessing herself proclaimed sins to a Catholic priest. She claims that sleeping with Chuck was a mistake and that she intends to avoid him. As she leaves the church and walks away, Chuck pulls up next to her in his limo and she tells him to go away. She says that she was practically given orders by God to stay away from him, and he asks her to do that over breakfast. Blair declines and tells him that she is going to the jewellers to put pieces on hold for her birthday. Chuck mocks her about Nate, and she makes her plans clear to fix her relationship with him. She reminds Chuck that Nate would probably stop being his best friend if he found out about the two of them. She uninvited him from her party, but he says that it's never stopped him before.While Blair waits at her party for Nate, Chuck talks to her. She mocks him, then asks if he likes her. He asks her to define like, and admits to feeling a fluttering in his stomach. She says that the butterflies have to be murdered. Not long afterward, Chuck finds Blair still on the roof and she admits her worries for why Nate isn't there. Chuck then talks to Blair about Nate's father's trial and how it coincides with Nate wanting to get back with Blair. They make the first of many wagers to come, the bets are that either Nate calls at midnight as it turns into her birthday as he has every year prior, or she spends the night with Chuck. Later, after the Gossip Girl blast showing a picture of Nate and Jenny hugging and Blair admitting that they broke up, she rushes to a room, very upset. Chuck goes to her and gives her the necklace that he bought from the jewellers, the one that she thought that Nate had picked up. Serena walks in on the two passionately kissing, before leaving unnoticed.
In Hi, Society, it is shown that Chuck and Blair continue a secret, physical affair. They are interrupted by Nate arriving at Blair's penthouse asking for her to go to the debutante ball with him. Chuck listens from another room, and it is obvious that he is jealous. He then spends time with Nate, telling him that Blair was dating Carter Baizen which was a lie. His intent was for Nate to get jealous and cause a scene, ending with Blair being mad at him. However, after Nate punches Carter at the ball. Blair finds out that Chuck had been the reason for the fight, and she tells him that their relationship was over. Later, Chuck watches as Blair goes into a room with Nate, where the two have sex. This breaks Chuck's heart so he leaves the country.
When Chuck returns he is shown as jealous, threatening to tell Nate about his relationship with Blair. Blair challenges him, saying she would like to see him try. Vanessa Abrams, in Chuck's favor, catches this conversation on tape while filming a documentary for a project. Trying to make it up to Blair, Chuck buys the tape from Vanessa for ten thousand dollars. However, this tape is actually blank, and Vanessa gives Blair the real one for free.
In A Thin Line Between Chuck and Nate, it is revealed that Blair may be pregnant with Nate or Chuck's baby. When Blair refuses to take the test, Serena tells Chuck to try to get him to convince Blair to take the test. Blair discovers she is not pregnant. Chuck is hurt she is still with Nate and blogs to Gossip Girl about there affair. Everyone takes pleasure in Blair being dethroned and when Nate finds out about Chuck and Blair's affair, the two argue and Nate tells Chuck to stay away from him. Nate also breaks up with Blair. When Blair goes to talk with Chuck, he tells Blair that he wants nothing to do with her and their relationship remains estranged until towards the end of the season when Chuck, Blair and Nate team up to help Serena.
Blair and Chuck work together to personally hunt down Georgina Sparks, an ex-friend who has been tormenting Serena for weeks and trying to seduce Dan.The next morning, Blair wakes up to find that she and Chuck fell asleep on her bed while plotting against Georgina. Blair pushes Chuck out of her room, not being able to acknowledge how she feels about him.At the Bass-van der Woodsen wedding,she and Chuck reconcile when Chuck announces in his best man speech that he intends to fight for Blair. Blair is moved by his words, which were inspired in the moment. The two share a kiss after he apologizes for his previous indecencies. Blair is surprised to see Chuck so romantic. A week after the wedding, Blair and Chuck prepare to spend the summer together in Europe. However Chuck, fearful of maturing and committing to a real relationship after a conversation with his father, backs out and leaves Blair waiting on the heliport, leaving her to fly off to Tuscany without him.
In the season two premiere Summer Kind of Wonderful, we learn Blair has stayed in Europe over the summer. Chuck stayed in the Hamptons trying to get over Blair by sleeping with a different girl every day. When she returns, he realizes that he regrets his actions; however, it is too late, Blair has begun a relationship with Marcus Beaton, a British lord whom she met in France. At the Vitamin Water White Party, while Blair is waiting for Marcus to pick her up, Chuck reveals that he was afraid that if they spent the entire summer together, she might see who he really is. Blair then says that she forgive him and commit to him and him only, if he tells her he loves her. He ultimately can't expose himself in that way and Blair leaves with Marcus.
In Never Been Marcuse, Blair throws a spontaneous back to school party where Marcus can bring his mother, the Duchess Catherine Beaton so the two can bond. Chuck tricks Blair into insulting the Catherine, hoping to ruin Blair's chances at a future with Marcus. However, Blair catches her kissing Nate and blackmails her into giving her approval. In The Dark Night, Chuck is having problems with his sexual performance and notices he won't be cured until he sleeps with Blair. During a blackout at a party, Chuck asks for Blair to sleep with him only one time but Blair refuses, even though Chuck notices she doesnt stop holding his hand. During a blackout that same evening, Chuck pretends to be Marcus and the two kiss passionately. When Marcus walks in on them and confronts the two, Blair admits she knew it was Chuck all along. Later Chuck is kissing some woman back in his limo but eventually tells her that he can't do anything with her, as he isn't over Blair yet.
In The Ex-Files, Vanessa discovers Marcus is sleeping with Catherine, and tells Blair. This ultimately causes Blair to end her relationship with the lord. Later, Vanessa tries to blackmail Blair by threatening to release the pictures of Marcus and Catherine to Gossip Girl, in an attempt to make Blair endorse her campaign to save an old bar. Blair enlists the help of Chuck to seduce and destroy Vanessa so she can never bother her again. However, in the midst of the proceedings, Chuck grows to like the old bar and Vanessa, so he backs out on their plan. Blair berates Vanessa anyway, and tells Chuck that he humiliated Vanessa enough to claim his prize: a night with her. When coming to collect, Chuck demands that she admit she loves him, as she had asked him to do before, but Blair adamantly refuses, telling him that she will never say those words to him. He gets up and leaves, telling her that he is done chasing, and it's now her turn to chase him.
Similar to Chuck's intimacy issues, Blair becomes obsessed with getting Chuck to sleep with her. Blair refuses to say that she loves him while walking to school. Serena invites Dan to give a little advice, and Dan suggests that Blair make herself irresistible to get Chuck to sleep with her. At one point, Blair entices Chuck into getting a drink with her; she throws herself all over Chuck by first getting him to smell her perfume and then "accidentally" spills her drink on Chuck's pants. Chuck gets bored with her desperate acts and leaves. She then calls Dan who suggests she intercept him at home. Blair goes to Serena's room, pretending to be there to have a sleepover. Blair nearly succeeds but their foreplay is interrupted by Serena's text message, where Chuck sees Blair is just trying to seduce him. He leaves, realizing that Blair was just playing games.
In her last effort, Blair takes Dan's advice once more and plans to admit to Chuck that she loves him. She calls Chuck, and asks him to meet her at the roof of Rufus' gallery during an opening. But before the meeting, Dan finds out about Vanessa's incident with Chuck and Blair and sabotages Blair by replacing his advice on taking risks with that of taking caution. Chuck and Blair get into an argument and Blair reminds Chuck that she asked him to say it first.Chuck walks off and Blair leaves the gallery. Later that night, Blair receives a visit from Chuck, who tells her that the reason that they can't say I love you to each other is because it would end their current relationship and send them to a closer level, one that Chuck knows they aren't ready for. Blair contemplates Chuck's advice, and eventually agrees, with the idea that they will put their relationship on hold.
In the episode There Might be Blood Blair has to babysit the daughter of a woman who is friends with the Dean of Yale hoping to get another chance to get in. The daughter, Emma, is determined to lose her virginity before one of her friends does. So Blair brings her to Serena's house and attempts to trick her into coming to a gala making her think that there will be lots of boys. Chuck ruins this plan when he comes and tells Emma that the gala is full of old people and goes off with her in his limo. She attempts to seduce him but fails, and runs off. When Blair finds out she's gone, she enlists Chuck and Serena to help find her. Chuck helps out by having Gossip Girl send a fake tip saying that the other girl lost her virginity so that Emma will give up. While Blair is walking Emma inside she tells her that she does not want to lose her virginity like that, it should be with someone you love. Emma asks Blair if she lost hers to someone she loves, and Blair says yes.
In It's a Wonderful Lie Blair and Chuck make a bet that they will find each other the perfect date for the snowflake ball. If Blair likes her date, Chuck gets Dorota for a month and if Chuck likes his date, Blair gets his limo for a month. While Blair is giving Dorota adjectives to describe the perfect girl for Chuck, Dorota comments that those are Blair's qualities. When they introduce the dates to each other, they realize they only succeeded in bringing people just like themselves. Chuck and Blair go off together to talk after they see their dates and when they get back their dates are hooking up. Blair then gets frustrated that even their doppelgangers can work it out and they can't. Later on Chuck says that even though they might not be like them he would not want to lose what they have. He then leads her onto the dance floor.
In the episode O Brother, Where Bart Thou?, Chuck reels from the news of his father's death. Blair forgets all their games and does what she can to be there for him. Nate notices that Blair is acting loving and maternal towards him, but she denies it. Later, Chuck goes to leave the funeral reception but Blair chases him down. She tears up and tells him that she will stand by him through anything. When Chuck asks her why would she do that, Blair finally says she she loves him. Chuck, being in such a troubled state, blows off her words and leaves Blair is left crying on the street.At the end of the episode, Chuck goes to Blair's and they spend the night together, in which she comforts him until they fall asleep.When Blair wakes up in the middle of the night. Chuck is gone, but left her a note saying she deserves much better and not to come looking for him.
During the episode In the Realm of the Basses, Chuck returns along with his uncle, Jack Bass, and initially shuns Blair. Blair still stands by Chuck when he goes back to St. Jude's, even making Headmistress Queller notice how troubled he is by Bart's death. When he is drunk and on the verge of suicide, Blair arrives and talks him down from a ledge. After telling Chuck she'll always be there for him, Blair shares a moment of affection with him. When her and Jack help Chuck get home, she asks Jack not to tell Chuck about what happened between them on New Years.
In the episode Gone with the Will, Chuck is given the job of becoming the new CEO of Bass Industries. At first Chuck willingly decides to give the job to Jack, who wanted the position more than anything else on the will, but Blair and Nate persuade Chuck to reconsider believing that he could do it, especially after hearing a letter Bart left for Chuck. Jealous and furious, Jack arranges Chuck to be caught by the board of Bass Industries, drunk, with a room of prostitutes and lines of coke lying around. When Chuck realizes what his uncle had done he storms out the congratulatory party arranged by Blair. Blair goes after Chuck but he tells her to stop acting like his wife. That night Chuck tries to apologize to Blair but she couldn't forgive him for what he said. This puts their relationship on hold once again.
In the episode The Grandfather, Blair is devastated of what has happened to her life, including being rejected by Yale, so she goes to Carter Baizen for help. Carter encourages the worst in her by getting her to let loose and she begins to change into a new Blair. At the same time, Nate's family, the van der Bilt's, are celebrating their family anniversary. During the party, Blair, having nothing to lose, decides to insult anyone who comes into her path, from cheating husbands to wives with bad face lifts. Serena and Chuck try to silence her to no avail. In a separate room later, Blair propositioned Chuck, but Chuck wouldn’t give in, claiming that this wasn’t the Blair he wanted. Meanwhile, Blair continues to stoop to new lows, and ends up escaping the party to a large silent room in the mansion. She is found by Nate who comforts her. Afterwards, Chuck goes to the Waldorf's to speak to Blair privately, but is sent away by Dorota. Before he leaves, he sees Nate's jacket and realizes he's upstairs with Blair.
In the episode Remains of the J, Blair and Nate start up a friendship; however Chuck is adamant that they are much more than just friends. Jealous, Chuck confronts Blair to which she replies that her and Nate's relationship is purely platonic. Chuck claims that Blair and Nate don't have any sparks, and that Nate is not over Vanessa, prompting Blair to claim that her and Nate have plenty of spark and fireworks. Chuck reminds her of their undeniable chemistry, saying that it was them who had fireworks, aggravating Blair, who then proceeds to explain that she fought for him, hard and for a long time; and that now that they are over, she is exhausted. She explains that being with Nate is easy and right. Chuck then teams up with Vanessa, who is now broken up with Nate, to drive Blair and Nate apart. Chuck and Vanessa arrive at Jenny's 16th birthday party together and walk in to see Blair and Nate sharing an intimate conversation. In the heat of the moment, Vanessa pulls Chuck in for a passionate kiss. Determined to prove Chuck's theory that her and Nate have no sparks wrong, Blair drags Nate along into Chuck's bedroom, and locks the door. Nate rejects her and she leaves. However they later share a kiss at the park and begin dating again.
Chuck later runs into Blair on the street and they begin plotting against Serena's new boyfriend Gabriel (who turns out to be a con artist). Jealously, Nate asks Blair to move in with him, but Blair doesn't answer, which leads Nate to confront Chuck about his constant proximity to Blair - he says that if he wants her, he should man up and tell her, and if he doesn't, he has to cut her loose, because Nate wants her himself. Right after that, Chuck decides to talk to Blair. She tells him she can't answer Nate's question, until Chuck tells her how he truly feels about her. Blair says that if he doesn't love her, he has to let her go, and begins to cry. He tells her it was just a game, and Blair walks away thanking him. Serena witnesses this conversation and when she questions him about it, Chuck tells her that he loves Blair but he wants her to be happy, and he believes that can't be possible if she's with him.Blair goes to prom with Nate but she sees Chuck with a lot of ballots voting for Nelly Yuki for prom queen. Blair believes Chuck wanted to ruin her but later it's revealed that he was just taking out the ballots for Nelly Yuki and instead voting for Blair so that she could have the perfect prom and be queen. Blair later breaks up with Nate as she feels he is still just her high school boyfriend.
In The Goodbye Gossip Girl, Blair and Chuck almost get together, but they don't as Gossip Girl publishes the blasts saying that Blair slept with Jack in New Year and that Chuck slept with Vanessa. After the blasts, Blair tells Chuck again that she loves him and if he says it back, all of the gossip and lies and the hurt would have been for something. Chuck only says that maybe it was, but not anymore. He walks away, and Blair starts to cry. A week after the reveal, we learn that Chuck left for Europe to figure things out. At the end of the last episode, Chuck comes back and explains to Blair that she was right and that everywhere he went, she caught up with him. Chuck apologizes and finally says he loves her too.They start kissing while Chuck keeps telling Blair that he loves her.
In Reversals of Fortune, Chuck is first shown flirting with a woman but Blair catches Chuck before anything happens and makes the girl go away after humiliating her. It's revealed that it's a game they play to keep things interesting: they choose potential girls who they want to victimize so that Chuck seduces them and Blair discovers them just before they actually kiss. At the same episode Blair is sure that Chuck is cheating on her but when she storms to his hotel, Chuck is alone. Blair says to him that maybe they need games and maybe without them they are boring. Chuck says that they can never be boring and that he's not Chuck Bass without her. Their game ends and they start role playing with each other. Chuck warns Blair in The Freshmen not to try to become a queen at NYU as it is not Constance. Blair wants to live at NYU for a while as she establishes herself as queen, in spite of Chuck's warnings not to try to become queen at college, and saying that lighting in the dormitories is horrible. After Georgina plays her old tricks, Blair is left alone at NYU, being rejected even by Dan Humphrey. She goes back to Chuck and instead of telling him about everything, she tells him that he was right about the lighting. <p>Chuck begins to be immersed in his work. He becomes too busy to spend quality time with Blair, blowing her off to get ready for a meeting with Sean McPherson, the owner of a hotel club Chuck wants to buy. At this meeting Chuck is given the cold shoulder from McPherson's assistant Daphne, who tells him that in order to even get his foot in the door, he must demonstrate respect for McPherson's past. He sees a Soethby's catalog with a photo flagged and decides the best way to get in McPherson's good books is to bid on and win the photo for him. Only it turns out that Blair needs the same exact photo in order to be accepted into a college society. As a result, Chuck and Blair have a bidding war for the photo at the auction until Serena ends up outbidding them in an attempt to get revenge for their sabotage on her boyfriend, Carter. Serena ends up giving it the photo to Blair, who then gives it to Chuck. She tells him that she believes in him. At McPherson's office the next day, Chuck deduces that Georgina set him and Blair up to go for the same photo, and Daphne, the assistant, who is also friends with Georgina, confirms it. He hands the photo to the head honcho and then leaves. Chuck tells Blair that, as she believes in him, he's ready to think a lot bigger - he's cashing out his shares of Bass Industries and is going to buy the whole entire Empire Hotel, not just the part he wanted to put a club in. He then invites her to go and christen the penthouse.
Chuck notices that Blair is dealing with her insecurity at not having friends at NYU by immersing herself in the Queen Bee drama at Constance Billard, her alma mater. When Blair denies it, he goes to Jenny for help. Chuck ends up bringing Jenny as his date to the movie premiere of "Fleur", causing Blair to be temporarily humiliated. When Blair shows up at the premiere to let Jenny have it, Chuck confesses that it was all his idea. He says he did it because he thinks she is selling herself short and needs to remember she's Blair Waldorf. If she can make Chuck Bass admit he loves her, she can win over NYU in due time. He also paid a photographer to take pictures of Blair at the premiere so that she would get her confidence back. Chuck also sends a school girl outfit to Blair's penthouse, with a note telling her that he needs some tutoring.
In episode Enough About Eve, Blair's plan to get to toast at the Freshmen Dinner during Parent's Weekend involves re-instituting her and Chuck's game from the summer… with a little twist. Blair tells Chuck that she needs him to seduce Josh Ellis so she can humiliate him, as he double-crossed her, and Chuck goes along with it. Blair interrupts them right after the kiss and pretends to make a big scene. In reality, she had made a deal with him; she gets to make the toast, and he gets to kiss Chuck. Chuck's plans get canceled, so he shows up at the dinner and gets a little too much info from one of Blair's new minions. Then he sees Blair and the man he kissed talking and laughing and he realizes something is definitely up. Blair's plan is revealed when Vanessa hides a microphone in her purse, and her nasty rant about Vanessa is aired to the entire audience, including how she used Chuck to get the speech. Blair goes over to Chuck's to apologize and it is clear he needs some more time to think about it.
In How to Succeed in Bassness, Chuck and Blair are talking again, though he is still chilly towards her. Chuck is trying to find a way to boost his hotel's ratings and decides to open the club. He calls Serena for help, as she works for a publicist and has PR experience, but instructs her to leave Blair out of it, not knowing that Blair is listening to the conversation. Blair calls Jack Bass and gets him to send over a liquor license for Chuck, desperate to help out. Later, Chuck comes to Blair's and gives her a costume for the club's opening, a flapper dress for the event's 20s era Prohibition theme, and they briefly make up. This is ruined when Chuck finds out she called Jack. Chuck tells her that he kept her out of opening the club for the same reason it took him so long to tell her he loves her; he can't trust her. He uninvites her to the opening but Blair shows up anyway after finding out the liquor license Jack sent over was a fake. Blair apologizes to Chuck and tells him that she was trying to make him see that he needed her. Chuck tells Blair that he already knew the license was a fake, and the two quickly come up with an idea. Chuck calls the police and has them shut down the club, while Blair makes sure the paparazzi gets pictures of the celebrities present in order to make the front page news and maximize publicity. Chuck decides to open a secret club, and by the end of the episode Chuck and Blair have made up.
Blair tries to keep Chuck calmed during The Debarted, as Chuck is deeply affected by the anniversary of his father's death. He starts having hallucinations in which Bart appears telling him he is a weakling for giving his heart to Blair. When Serena gets in a car accident due to running off with Nate's cousin Tripp van der Bilt, Chuck goes to the hospital and lies on the floor overwhelmed by the memories of finding out Bart was dead. Blair keeps him company in there and offers supportive words and also encourages Chuck to go visit Bart's grave. When Chuck does so, he sees a woman crying at the grave with yellow roses, which were Chuck's mother's favorites. Chuck investigates the woman to find out if it is her mother but the woman denies it. Blair realises the woman is lying and tells her to decide if she does or does not want a relationship with Chuck, but not to string him along. Elizabeth, the woman later reveals that she Is Chuck's mother and starts bonding with Chuck.Jack Bass hatches a scheme to take control of Chuck's hotel. Jack makes Chuck appear in a sex scandal and Chuck has to give somebody the title of owner of The Empire temporarily, as to not hurt business. Chuck gives the title to Elizabeth as Blair convinces him to trust her. It's later revealed that Elizabeth handed over The Empire to Jack, whom she loves. Elizabeth leaves town after telling Chuck that she is not his mother, even though she is, because she feels too much guilt for what she has done.
Later, in Inglourious Bassterds, Jack asks Chuck if he wants the hotel back he can: in exchange for a night with Blair. Jack runs into Blair and tells her that a night with her is the only price for the hotel, and that Chuck wouldn't even mention it to her because he wouldn't risk losing her. Blair sees that Chuck is crushed, and after Jack sends her a dress telling her it is her last chance to save Chuck's hotel, Blair goes to Jack. Jack kisses Blair but then reveals that Chuck and him had planned the moment in which Jack ran into Blair, and that Chuck's desperate act had been played in order for her to feel compassion and to go to Jack. Blair is devastated as she now knows that Chuck traded her for his hotel. Jack tells Blair that he does not need to sleep with her and Blair leaves to her penthouse. She finds Chuck in the lobby and they have a fight. Chuck reminds Blair that she told him last year that she would stand by him on the worst thing he could ever do, but Blair tells him that she never imagined that the worst thing he'd ever do would be to her. Chuck tells Blair that even if he did wrong, Blair went to look for Jack on her own. Blair slaps Chuck in the face and leaves him.
In The Unblairable Lightness of Being, Chuck doesn't want to give Blair up and throws a traditional Polish wedding for Dorota and Vanya. Chuck lies to the people saying that Blair and him are back together, so Dorota asks Blair and him to be the "happy couple" to escort them on their wedding for good luck and Blair has to accept. Blair is too embarrassed to say what Chuck did to her, and only tells Nate, who gets in a fight with Chuck over what he did. Chuck says to Blair that she has to forgive him because he loves her. Blair later tells Chuck that he was right, that they are meant to be together as they are both sick and twisted. She tells Chuck that they are incredibly fortunate to have even found each other but Chuck tells her that he doesn't want her to settle, and him to be some sort of consolation for her. During the wedding, Blair can't deal with it and breaks into tears, telling Dorota that Chuck and her can't be the happy couple as she is miserable with him. Chuck begs Blair to stay with him and to not end their relationship but Blair replies that this is the end and thus ultimately ending the relationship, causing him to go back to seducing any woman he desired, only to get over how devastated he is.
When Jenny and Chuck suspect there is something wrong with Lily's medication they go to Blair, but she refuses to get involved in a scheme with Chuck as she is going to have a date. During Blair's date, Dan and Nate appear, looking for Blair's help in a scheme to prove that Rufus was not cheating on Lily and Blair agrees to help them. The schemes lead both Blair and Chuck to discover that WIlliam Van der Woodsen is giving Lily fake cancer so she'll fall for him and they have to work together. While distracting the psychiatrist working with William, who is also the woman who pretended to be having an affair with Rufus, Blair and Chuck ask her help, and they tell her all their problems, including how Blair was traded for a hotel and how Blair made Chuck kiss a guy.After the entire scheme of William is exposed, Chuck tells Blair that he did to most dangerous thing when he said he loves her but it was worth it and on the next day, he would be waiting for her at the top of the Empire State Building. He tells Blair that if she hasn't arrived by 7:01 he will close his heart to her forever.
In Last Tango, Then Paris Blair tries to keep herself far from the Empire State so she goes to Brooklyn. Dan asks her if it is wrong to avoid signals from destiny, and even though Blair tells him that signals are only for the superstitious, religious, and the lower class, she decides to go to the Empire State when she sees it from underneath the Manhattan Bridge. when she is getting in the car, Dorota's water breaks and they have to go to the hospital. Blair arrives late to the Empire State to find out that Chuck has left, but she knows that he was there because she find peonies in a trash can.
Chuck, thinking that Blair doesn't love him anymore, goes back to The Empire and gets drunk. Jenny arrives and is looking for Nate. Chuck says to Jenny that he did the most romantic thing that he could think of but it didn't work. Feeling rejected, Chuck sleeps with Jenny. After they sleep together, Chuck asks if she wants to spend the night. Someone arrives and it's Blair. Blair asks Chuck is someone in his room but he says no. Chuck is confused because he was sure that Blair didn't want he see him ever again. Blair shows him the peonies from the Empire State and tells Chuck that she was late because Dorota had her baby. She also tells Chuck that she followed her heart because she loves him. She also tells him that in the end, love makes everything simple. They hug and Chuck is happy but is seen watching his bedroom with regret. Jenny is still hiding in Chuck's room and sees something on Chuck's bedside table. She opens the bag and inside finds an engagement ring. Chuck says to Blair that they need music. He goes to his bedroom but Jenny has left. In the hospital, Chuck says to Blair that he's sorry about everything and he wants to spend rest of his life making it up to her. Chuck is about to propose to Blair, but Dan who has find out about what Jenny and Chuck arrives and punches Chuck in the face. Blair is first confused but quickly realizes that Chuck slept with Jenny and she exiles Jenny forever from Manhattan. When Jenny and Dan leave with Rufus and Lily, Serena asks Blair if she is okay and she gives a faint smile. Blair and Chuck are left alone and Chuck starts apologizing by saying Jenny Humphrey was a mistake and says that he thought Blair didn't love him anymore but Blair tells him not to say her name or anything else to her ever again. Blair tells Chuck that the night never happened and leaves the hospital. Chuck is devastated once again.The season ends when Chuck is in Prague drunk and upset. He is assaulted and the thieves try to steal something from Chuck. He fights for the thieves not to steal it and he gets shot. The thieves leave the scene after stealing what Chuck was protecting: the engagement ring.
Season FourThe season begins with Blair and Serena in Paris. Blair is troubled after a Gossip Girl blast announces that she has had a summer without any romance, so she makes it her mission to get a date to forget Chuck. Blair also informs Serena that Gossip Girl hasn't posted about Chuck all summer. Later, Blair is at an art museum when she is approached by a handsome man, Louis Grimaldi, whom she suspects is a member of the royal Grimaldi family in Monaco. She agrees to a double date with him, Serena, and Louis' friend Jean Michele. During their dinner date, Louis pretends Jean Michele is the royal one in order to test Blair and see if she's only interested in Louis' title. The date fails, and Louis realizes that is all she's after. At the chateau afterwards, Blair tells Serena that that she has been able to fake being okay all summer, but in reality she is not over Chuck, and she is worried that she never will be able to move on. At the end of this episode, Chuck is shown with a woman who saved him after being shot. He is living with a fake identity as Henry Prince and he and Eva are in Paris.
In Double Identity Lily is called by the police because a body has been pulled from the Sein river in Paris, and said corpse is found with Chuck's ID. Lily asks Serena to go identify the body, and Serena is worried about telling Blair, who is on another date with Louis. While in the car on her way to see Louis, Blair sees Chuck, she tells the driver not to stop for pedestrians and they just look each other without saying a word. Serena later tells Blair that she had to go identify a corpse but that thankfully it wasn't Chuck, but he is indeed missing. Blair tells Serena that she already knew Chuck was alive and well because she had seen him earlier that day. Serena tracks down Chuck's place in Paris, but he is with Eva and pretends not to know her. When Serena goes back, she tells him that he need to come back or he'll lose everything, including The Empire and everything his father left him, Chuck says that he already has lost one thing that mattered (Blair), so they can have everything else. When Serena goes to see Chuck again he has already left with Eva. Serena knows he is intent on disapperaing and that the only person who can stop him from leaving is Blair. Serena tries to convince her to go save Chuck. Blair is reluctant to help because she is on her way to a royal ball to meet Louis' family. On the way to the ball, Blair stops by Harry Winston. She is admiring a beautiful diamond engagement ring, and the clerk informs her that it has already been purchased. Serena arrives with the detective involved with Chuck's case, and explains that when Chuck was shot the muggers took the ring but were unable to pawn it in their usual places. They tried to return it to the shop for cash but Harry Winston knew Chuck had purchased it and called the police. Blair is surprised to hear that Chuck was going to propose to her and that he was shot, and seeing the ring convinces her to go after Chuck. She finds him at the Paris train station. Blair tells Chuck that changing his name won't change who he is. Chuck tells her he wants to be a better man, and that her world would be much easier with out him. He feels as if he has destroyed the only thing he has ever loved, but Blair says that it takes more than even him to destroy Blair Waldorf. Blair shows Chuck that she has the ring and gives it back. Blair is tearing up and she says to him that she doesn't love him anymore. Blair tells him that although life without him would be easier, it wouldn't be her world without Chuck in it. Chuck is convinced and decides to go back to New York. Chuck reveals his true identity to Eva and invites her to come with him back to Manhattan.<p>Blair hates that Eva is making Chuck happy and that he is parading her all around New York. In Touch of Eva, Blair is working to find something to cause Eva and Chuck to break up. After Chuck gifts Eva a Cartier watch, Blair films her selling it and shows the video to Chuck. Eva apologizes by telling Chuck that she gave the money to somebody who needed it and Ivan, an employee at The Empire comes forward and tells Chuck that Eva gifted the money to him. Chuck forgives Eva, and Blair decides that she has to dig even farther. Blair apologizes to Eva and tells her that she is still protective of Chuck, and goes with Eva to pick a charity for a donation Chuck will make. Blair asks Eva to tell her everything about her life, and has Serena and Dan investigate whatever she finds out. They find out by the neighborhood where she lived that Eva used to be a prostitute. Dan tells Nate, who tells Chuck. Chuck pretends to have already known, but confronts Eva about it before Blair can tell him on her own. Chuck forgives her, as she forgave Chuck for everything in his past.
That night, Chuck hosts a party to announce what charity he will honor with a million dollar donation, and before the announcement can be made Blair tells Chuck about Eva's secret. Blair is unsuccesful in her attempt to break them up, as Chuck already knew, so she steals Chuck's passport to make it look like Eva knew who Chuck was all along and that she was a gold digger. When Blair shows the passport to Chuck, Chuck tells Eva to get out. Blair feels guilty because Chuck is so devastated, he goes on to tells her that he was stupid thinking somebody good could actually love him. Later thanks to Lily, Chuck finds out that Blair tricked them, and that Eva was truly a noble woman. Chuck runs and apologizes to Eva but she refuses to listen. She tells Chuck that he chose to believe Blair, and tells him that she can feel the bond between Chuck and Blair, so she leaves. She tells Chuck that he is a good man and to never forget her. Chuck goes to Blair's penthouse and asks her if she could have acted so selfishly because she still loved him. Blair denies her feelings for Chuck, so Chuck is convinced that Blair ruined his chances at happiness out of hatred for him. Blair also denies this, but Chuck doesn't believe her. Chuck declares full war.
In the next episode Chuck is determined to take everything away from Blair, because she took away his future. Chuck also says that watching Blair suffer will make him happy. Blair tells him that the only thing that will make him happy, he lost the moment he slept with Jenny. This gives Chuck an idea and he makes a call and Jenny Humphrey comes back in town.
Jenny Humphrey's return turns out to be mutually detructive to both Chuck and Blair when she reveals via GG how she lost her virginity to Chuck. Blair and Chuck are both humiliated by this blast. They start fighting, but Jenny interrupts them, by telling them that when they were together, they were invincible but now that they're enemies, their mutual destruction is inevitable. At the end of the episode, Chuck comes to Blair's and they agree that what happened was tragic fate, but that it happened and they make a truce. In War at the Roses Nate and Serena sit Blair and Chuck down and help them make a legally binding peace treaty.
As an additional gesture of trust, Blair invites Chuck to her 20th birthday party. Dan and Eric want Jenny to come home for Rufus and Lily's anniversary, and the only way that can be achieved is by making Chuck angry enough to help Jenny back into the city. Dan sends a fake tip to Gossip Girl about Blair sleeping with Jack, and plans to stage a run in with Chuck at The Empire. When he arrives, he's surprised to find Blair there. They explain that they knew one of their many enemies would try and mess with them but they both know the blast was false. Chuck seems to get a little jealous when Blair tells him she knew that Jack was in Chile last summer. At the party, Blair and Chuck get into a fight because someone released an embarrassing video of Blair singing karaoke to humiliate her. Blair is sure that it was Chuck and asks him why he would do that to her. They fight and Chuck insists he is innocent, then Blair reveals to Chuck that she only knew that Jack was in Chile because she was looking for Chuck but no one could find anything on him, only Jack. Later it's revealed that Dan released the video to get even with Chuck and Blair for driving Jenny out of town. At the end of the episode, Chuck and Blair agree that their treaty is not working out. They both claim that it will not work because they can not be friends because they hate each other so passionately. Chuck rips the treaty, then grabs Blair and they start kissing, this leads to passionate sex.
In Juliet Doesn't Live Here Anymore, Chuck and Blair have been having a lot of hate sex. Serena finds out that they have been sneaking around and warns Blair that it is impossible to act so casually with Chuck because they have so much history. Blair thinks the best way to avoid sex with Chuck is by going on a cleanse where she avoids him, but Chuck thinks they need immersion therapy where they have so much sex they won't want to anymore. He almost has Blair convinced, but then she takes off for the ballet. At the ballet, they team up to defend Serena against Juliet. After the take down, Chuck and Blair sip champagne in her apartment celebrating their victory. They try telling each other they are friends, but as Chuck leaves, they share a tender kiss, and Chuck carries her up to her room.
During the ninth episode titled The Witches of Bushwick, they are both told a relationship with the other one would be disastrous for their future plans, so they decide to keep their "friends with benefits" relationship a secret. Chuck accidentally tells Blair he loves her while they are about to have sex. Not knowing if he meant it, she tries to ignore it, but cannot resist going to his Saints and Sinners party to ask him about it. He tells her he meant it, with all of his heart. She tells him that she loves him too, and they kiss passionately in front of everyone at the party. Blair loses that chance at being the face of Anne Archibald's foundation because of her relationship with Chuck. She decides that she needs to be Blair Waldorf before she can be Chuck Bass' girlfriend. Chuck is very understanding. She also tells him she doesn't expect him to wait for her, but Chuck answers that if they're meant to be, they'll find their way back.
On Thanksgiving in Gaslit, Chuck and Blair run into each other at Serena's house, Chuck offers to leave but she tells him that she was heading to JFK anyway to head for Paris but came to drop off the traditional pie and that they should get used to run ins. They hear about Serena being hospitalized and while they're sharing that maybe nothing can change between them, Jenny walks in and their conversation is interrupted. While driving Blair home, Chuck tells her that he showed up only for Serena when she told him that what happened with Serena made her question what she told him after the Saints & Sinners party. Chuck tells her that he cannot be her friend now as much as he wishes he could. But even after that Blair still sends him a pie along with a card, stating that just because they can't be friends doesn't mean they aren't.
They remain friends and they even ask each other for help if they need it. When Chuck meets a woman named Raina Thorpe, he's trying to make her fall in love with him so her father Russell will spare Bass Industries. Chuck needs Blair's help with Raina, saying that it's only for business reasons. Chuck is also falling for Raina, unbeknownst to Blair. On Valentine's Day, Blair asks Raina if she can be shadowed for an article for W Magazine, and she agrees. When Serena learns that Chuck is starting to fall for Raina, she tries protect Blair and tells Raina that she needs to kill the story because Blair still has feelings for Chuck and if she follows her and Chuck on Valentine's Day, she's going to be hurt. At a Valentine's Day party, Raina and Chuck have a fight, which Blair accidentally overhears. Raina tells Chuck that nothing is sacred to him, and Chuck answers that she's wrong, and that she is sacred to him. Raina walks away from Chuck. Blair is heartbroken when she realizes that Chuck honestly does have feelings for Raina.
When Russell informs Chuck that Bart was responsible for his wife's death, Chuck is devastated. He explains to Serena that all he ever wanted was for his father to be honest with him, but all he got was lie after lie. He decides he needs to find Blair because she's the only one who would understand. However, Blair is trying to navigate her feelings toward Dan, and the two share a brief, life changing kiss. In The Kids Stay in the Picture, Chuck confronts Blair about the kiss, but she says that it was life changing, because it make her realize that she wanted it to be with Chuck. Later Blair tells him that now that she knows she's ready to build a future with him, she realizes that Chuck is not ready. She says that she's sorry and walks away.
Soon after this Prince Louis comes to the Upper East Side to find Blair and the two begin to date. Their relationship moves very fast, but Chuck is convinced Louis is just a distraction and that he is her true soulmate. Blair is set to attend a ball along with other women Louis' mother wants him to consider marrying. Chuck, wanting to win Blair back, takes the engagement ring he bought for her to the ball and crashes. He causes a scene and Princess Sophie Grimaldi throws him out. When Louis proposes that night, Blair accepts, excited to finally get her fairytale. She goes to Chuck to announce her engagement, enraging her already-depressed and intoxicated former lover. Chuck loses himself, and grabs Blair and punches a window after she says it's over, and the shards cut her face. She then runs from the room with a small cut on her cheek. In the next episode, Jack comes to town and soon as Blair sees him, she goes to warn Chuck. However, Louis' mother Sophie has her followed and tells Louis that the first place she went after they got engaged was to see Chuck, and Louis catches her seeing Chuck again when she warns him.
As revenge for turning his daughter against him, Russell lures Blair into Chuck's new hotel because he knows that Blair is the one thing Chuck loves more than anything, even if they aren't together at the moment. Russell threatens to leave Blair in the building and light it on fire so a Bass man can lose his love the way he did. Thanks to Blair still having Chuck on speed dial, he is able to save Blair from Thorpe just in time. Later trying to calm her nerves, Chuck takes Blair to a bar mitzvah party. Blair realizes that she still has feeling for Chuck, so instead of leaving the party to meet Louis the two sneak into a back room and they have sex. After they have sex, Blair is convinced that she has to break things off with Louis. Although Louis makes her happy she knows Chuck is her true love and that as hard as they may try to let go, they are drawn to each other. Chuck is sure that he has to let Blair go, thinking her love for Louis is the right love. In a tearful good bye Blair tells Chuck she will always love him, and he tells her that he feels the same. He watches her walk away with Louis. When the summer is about to start, Blair is ready to plan her wedding with Louis while in Monaco and Chuck is about to go travel the world and have a lost summer with Nate. At the end of the episode there is a positive pregnancy test in the trash can of Blair and Serena's bathroom.==Season Five==
Season five kicks off with Chuck in Los Angeles with Nate and Serena. Chuck met a actress/stuntwoman, Zoe Bell, over the summer as he struggles to get over Blair, however their date comes to a quick ending when he appears to be unharmed after a motorcycle accident. He hires men to beat him up because he feels numb as a result of Blair choosing to be with Prince Louis, and hopes that pain will help him feel. The physical abuse still does nothing to help him feel anything. Dan then tries to make Chuck feel, by buying him a dog. Meanwhile, a newly pregnant Blair isn't sure if the father is Chuck or Louis. She takes a paternity test at Dan's insistence, only to find out that Louis is the father. Later, Blair goes to Chuck's apartment to tell him she's pregnant with Louis' baby, but she also tells Chuck that a part of her was hoping and wanting the baby to be Chuck's. This news devastates Chuck and he begins to feel again. <p>Chuck starts to see a therapist about his numbness, learning that it is a psychosomatic response to his emotional pain. However, his therapist is being bribed by Louis to drive Chuck into a rage and make Blair see that he will never be the right choice for her. When Blair finds out, she becomes upset at Louis and begins to doubt her choice. Later, we see that Chuck is trying to be a better person. During Blair and Louis' wedding shower, he crashes to stop an intoxicated Dan from ruining the festivities. Blair mistakingly assumes he wants to ruin the party and becomes upset. Afterwards he goes to Blair's house and apologizes for everything he did wrong in the years that they have known each other, and he's going to take care of himself from now on. This makes Blair continually doubt her decision to marry Louis. At the end of the episode I Am Number Nine, Chuck returns the engagement ring to Harry Winston that he has been holding ever since he was going to propose Blair in season three, in order to gain some peace and finally let Blair go.
Blair is not convinced of her former lover's change of heart. She wants to prove to herself that Chuck is still the evil person he always was and is only pretending to be nice to impress her. Blair goes to the performance of Sleep No More without Chuck knowing in The Big Sleep No More. She follows him throughout the night and finally finds him alone at a bar. She approaches him, locks the door and proceeds to try and seduce him.Blair plays coy, gets close to Chuck, brushes hair from her neck and teases him with red hot candies until Chuck breaks down and kisses her with passion. The scene is followed by Blair slapping Chuck square across the face. She says that his inability to resist her proves that he hasn't changed and that she knows for sure that she made the right decision to marry Louis. She ends her scheming and says that she will welcome Louis back from his trip to Italy with open arms. But Chuck actually has changed. With a tip from Dorota, he wound up kissing Blair so that she could move on with her life. Chuck knows that Blair would never be able to move on if she thought he really had changed into a good person. By her thinking that he's still the same old Chuck, he knows she can move on and be happy, or so it seems.
As she's trying to pull Louis from the dark place he has been as a result of his jealousy of Chuck, Blair spends a day with Chuck to see if Chuck really has become a good person. As they are in therapy, Chuck tells Blair that he returned the engagament ring to Harry Winston. Blair is hurt and leaves the session. Later, when Chuck comes to her penthouse, Blair apologizes about bringing Chuck's dark side out, and she now knows that she's the reason Louis is also becoming dark. Chuck tells her that she was the lightest thing that ever came into his life and that he just wants Blair to be happy, although he wishes that she could be happy with him.
Though she insists that she's in love with Louis, Blair is starting to fall in love with Chuck again. In Riding in Town Cars With Boys, at Dan's advice, Blair makes a phone call to Chuck to ask him if he could ever love another man's child. She explains that she is paralyzed and trying to make a decision. He tells Blair that he cannot make the decision for her. And he eventually tells her that marrying the father of her child Louis Grimaldi doesn't seem like a mistake. So Blair hangs up the phone and believes that her decision is made. She will marry Louis since Chuck basically told her not to break up her family. But as she tearfully tells Dan what happened, he devises a plan.
He takes her to Charlie's debutante party and sneaks her into a back candlelit room. Then Dan brings in Chuck and leaves both of them alone together to work things out. While together, Chuck confesses that he wants to be with her and that he will love her baby as much as he loves her. This seals the deal for Blair, who realizes that her heart really belongs to Chuck. But just as they are about to make plans for how to handle the situation and tell Louis, a Gossip Girl blast goes out that reveals their location. Blair knows that the place will soon be swarmed with the paparazzi and they make a plan to escape. Nate offers the couple his car that is parked in the garage downstairs and Chuck and Blair hop into the town car and flee the party. But the car that was originally intended for Nate has some mechanical problems. In the back seat of the car, Chuck seems both excited and flustered by Blair's decision to pick him. He wants to make sure that she's not having any regrets about leaving Louis. Blair assures him that he is the one that she has always wanted and that she loves him and he is the one she never wants to leave. But with paparazzi swarming the car, the driver loses control and Blair and Chuck wind up in a major accident. At the hospital following the accident, Blair becomes conscious, but Chuck remains in an unknown state and seems to be fighting for his life.
After the accident, Chuck is in a coma because he has lost a lot of blood and Blair has lost her baby. She makes a pact with God, that if God saves Chuck's life, Blair will keep her promise to marry Louis. Seconds later, Chuck wakes up and Blair is convinced that she has to keep her promise to God, because she's worried if she continues to see Chuck, something will happen to him. In the following weeks, Blair has difficulties staying away from Chuck, saying she feels dead inside without him.
In the 100th episode of Gossip Girl titled G.G. , it's Blair's wedding day. After seeing a distraught Blair, Eleanor convinces Chuck to come to the church and stop the wedding. He asks Blair not to marry Louis. Blair says that she loves Chuck, in fact she claims to love him more and more everyday, but they can't be together. Unbeknownst to either, Georgina is filming their conversation. Before the ceremony, Serena tells Chuck about Blair's pact. Midway through the wedding, the video is released by Gossip Girl of Blair saying she is in love with Chuck. Blair immediately leaves the ceremony and confronts Chuck, who denies sending the video in. He informs her that he knows about the pact and that he's still alive even though she ran away from the wedding. She then apologizes to Louis, and they continue their wedding. During Blair and Louis' wedding dance, Louis reveals that he no longer loves Blair but they most stay married in the public eye, and that behind closed doors, they are now strangers. At the end of the episode, Chuck heads to the wedding reception to try again with Blair and apologize but finds she is gone when he arrives.
In The Backup Dan, after realizing the mistake she has made in marrying Louis, Blair leaves her own wedding to flee to the Dominican Republic. She has Dan take her to the airport, and explains that she can hopefully secure an annulment there without Louis' consent, but she needs to do it before the Grimaldi's can stop her. At the airport, Blair is without her passport and the two go to a hotel to wait for Dorota to bring it. Meanwhile, Serena, Nate, and Chuck know Blair is missing and are desperately trying to find her before Louis and Sophie. Chuck and Serena get to the hotel before the Grimaldis, but they catch up soon after. Serena also takes the fall for sending the video into Gossip Girl, to allow Blair and Chuck to finally be together. Sophie reminds Blair that if she violates her marriage within the first year, the Waldorf family will have to pay the dowry, which is so much money they'll be forced to declare bankruptcy. After they leave, Chuck and Blair talk. Chuck tells Blair he loves her and will pay her dowry and do whatever it takes to protect her. Blair insists that their fresh start can't be him buying her from Louis, and she needs to do this so they can become equals.In the episode The Princess Dowry, Blair tells Chuck that she still loves him, and always will but she isn't in love with him the way he deserves. She also tells him that he no longer has her heart anymore, and she begins to date Dan.
Meanwhile, she desperately tries to find a way out of her love-less marriage, but it is nearly impossible considering that the amount of the dowry would bankrupt her mother's company. Chuck secretly pays her dowry, wanting only her freedom, and makes sure only his PI Andrew Tyler and Nate know. However, Nate accidentally lets it slip to Dan that Chuck paid the dowry, and he becomes concerned that's why she hadn't signed her divorce papers. He asks Blair about it, and Blair is surprised to find out he paid. She becomes very upset, claiming he has learned nothing since the time he tried to sell her for his hotel. She thinks he is trying to buy her back. Chuck insists that that was not his intent, he claims that he just wanted her to be free, including free to love who she chooses. At the end of the episode, she sends him a text message, thanking him for setting her free.
Blair and Chuck come together again in the episode Raiders of the Lost Art. Blair's plan is to head to the Met, to seek inspiration and find her true self, which she feels like she's lost- but on the way, she encounters Chuck, who asks her for help to uncover the truth behind Diana Payne pretending to be his mother. At first, Blair starts to refuse, but tells Chuck it is his lucky day after she receives a message from Dan cancelling their lunch plans. Blair and Chuck head to Blair's penthouse in which she changes into a tight dress to channel Diana Payne and tells Chuck that she has a cipher slide to break codes, as she once had to encode her diary to prevent Eleanor from reading it. She looks at the planner that Nate stole from Diana Payne and notices she always has a meeting at 9:00 p.m. on the first Saturday of every month,which includes that day. When Blair arrives at The Empire she gets called by Dan, who tells her he has been offered to spend the summer in Rome to get inspiration in order to write his next book. Dan is shocked because Blair tells him she would never stand on his way with such a great opportunity and that Dan has to go. Dan gets suspicious when Blair tells him she is scheming with Chuck. Nate, Chuck and Blair arrive to the place where Diana is supposed to go (which turns out to be a brothel).Chuck is offered company by one of the prostitutes, but Blair gets jealous and tells the woman that Chuck is with her. Chuck and Blair ask the woman to show them the house, in order to find a room to have sex in, but in reality they are doing reconnaissance.
When Diana spots Chuck and Blair, she calls security and the house starts to empty quickly. Blair enters a room and finds something that shocks her deeply. Later, Blair runs into Jack and tells him that she's going to tell Chuck what Jack is really hiding in the house. Jack tries to convince Blair not to tell Chuck because she would cause a lot of damage. Chuck finds a visibly upset Blair in the parking lot and asks her what's wrong and he assures her that after everything they've been through, there shouldn't be any secrets between them. She tells him that he should go inside the house when it is dark and emptied.
Gossip Girl gets her job back, as it is revealed Nate and Lola were helping her to overthrow Serena, and the first thing Gossip Girl publishes is about Blair heading back to Brooklyn. Blair arrives to Dan's loft and asks him if he is upset with her, but Dan denies it. Dan lies and tells her that he didn't get the internship in Rome, but Dan only rejected it out of fear that their relationship wouldn't survive long-distance. As Blair is about to leave, Dan tells Blair that he loves her, but she doesn't say it back. At the end of the episode, it is revealed that what Blair was shocked to find in the brothel was that Chuck's father Bart Bass is alive.
In the next episode, "The Fugitives", Blair is about to text Chuck how he's doing but Dan's agent calls and Blair answers. She finds out that Dan lied about Rome. When she brings it up to him, Dan tells her that he was worried about her and Chuck spending more time together again. Later, Blair runs into Chuck on the street and asks how he's doing. Chuck tells her that his father is about to leave again because some powerful people are after him. Chuck asks Blair if there's anywhere she has to be, and she gets in the car and leaves with him. When Serena calls Blair to find out where she is, she says she's with Chuck. Serena tells her that Dan has some news and she has to come right away. When Blair gets back, Dan asks her to accompany him to Rome for the summer. Blair isn't sure she wants to go, so she tells him that she will have to look at her calendar first, so she can buy some time to think. After thinking about it, Blair accepts but she doesn't seem enthusiastic about her decision.
As they are ready to meet some people involved with Dan's trip to Rome, Serena texts Blair that Chuck is in trouble and Blair lies to Dan and tells him that she has to go get gelato and that she will come back before the meeting begins. When Blair gets to Chuck and realizes she can't make it to the meeting, she sends Serena to go instead and Serena pretends that she is Blair. When Dan asks Serena where Blair is, she lies too and says that Blair is with her mother. Later, when Dan finds out where Blair really is, he's upset because Blair lied to him again. He admits to Serena that he told Blair than he loves her, but she didn't say it back. When Blair comes back, Serena tells her that maybe it's time her to tell Dan how she feels. Blair says she's not ready, and that the next time she says it to someone, it will be the last time. At the end of the episode, Dan asks Blair if she is sure that she wants to come to Rome with him and Blair says that she does.
In The Return of the Ring, Gossip Girl starts to release excerpts from Blair's diary, spanning her entire life. When an excerpt that reveals her concerns about not getting over Chuck, Dan gets jealous once again. Blair attempts to explain that the journal entry was from after their first disastrous attempt at sex, but Dan gives her an ultimatum: tell him how she feels, or she can't go to Rome with him. Soon after, Gossip Girl posts another piece from the diary entry from a year ago where she admits that Chuck deserves to be alone forever after selling her out. After that post, Blair goes to see Chuck at the Empire to make sure he wasn't upset by it. Chuck tells her that the diary entry doesn't matter because is was a year ago and that they have made amends since then. Then Chuck asks if she broke up with Dan, she says no and Chuck tells her that he's tired of playing this game, he spend a whole year waiting for her and he has to move on with his life. He asks her if she has anything else to say and she pauses, looking unsure, then she gets a text from Dan and says she has to go.
Blair realizes that she has to choose, Dan or Chuck. She talks with her mother and says that Dan is her best friend, and she feels safe when she's with him; and with Chuck she's vulnerable, but he makes her happier than she's ever been. Eleanor tells Blair that she is retiring from Eleanor Waldorf Designs and that her job as CEO is Blair's, if she wants it. Blair accepts, though admitting that she will have to hire designers since she isn't one.
Afterwards in the car, Blair calls her mother and tells her that she chose who to be with, and shows up at The Empire. At the same time, Bart publicly cuts Chuck out of Bass industries and he is devastated. In a private conversation, Bart tells Chuck that he can't be trusted with Bass Industries because he put Blair before the company, and all she did was toy with him. Shortly afterwards, Blair comes to tell Chuck that she loves him and wants to be with him. She explains that she's tried to run away and hide from her feelings, but she can't, and she doesn't want to anymore. An angry and teary-eyed Chuck rejects her, saying that he's lost everything, and he's tired of putting her first and having her bet against him. He needs a future, and he doesn't want to just be Mr. Blair Waldorf. Blair is left, in tears, watching him walk away from her, but this time, she doesn't give up on the man that she loves. In the final scene, Chuck is playing blackjack in Monte Carlo with Jack to win enough money to get back into Bass Industries, when Blair joins the game. Blair tells Chuck that she knows that he fought for her and she says that it's now her turn to fight for him, and she's all in. The dealer asks Chuck if he will be all in too. The season ends with Chuck and Blair gazing at each other.
In Gone Maybe Gone, it's revealed that Chuck and Blair ended up in bed together the night she came to see him in Monte Carlo. After several straight days of sex, which left them both exhausted and starving, they'd promised to be together after they took care of their own issues: Chuck trying to discover his father's secret and regain control of Bass Industries, while Blair is taking charge of her mother's company. When Blair and Chuck meet up at the end of the summer, Blair tells Chuck that she's still all in and Chuck responds that his bet is on them. During a conversation with Dan, he plants the idea that she made the wrong choice choosing Chuck because he will never be able to commit to her. He tells her that she's only committing to the idea of Chuck and the pact is a waste of time. In a poignant limo scene, we find out that Blair has been wearing the Harry Winston engagement ring on a necklace, as a token of their promise. Chuck tells her that the boy he was would have blamed her for his problems, but he wants to be a man now, for her. He promises her that she won't have to wait much longer for them to be together.
When Blair is in trouble with her first fashion show in High Infidelity, Chuck comes to her rescue. In the end of the episode, Chuck comes to Blair's bedroom to celebrate with the bottle of Dom, but Blair is upset that her very first fashion show was disaster. Chuck says that the clothes were beautiful and so is she, and that's worth celebrating. Blair tells Chuck that they need each other and Chuck agrees that if they help one another, the sooner they can be together. He tells her how Bart was meeting with someone named Lady Alexander in Dubai. Still keeping to their pact to remain platonic, Blair falls asleep in Chuck's arms.
In Dirty Rotten Scandals, we see that Chuck and Blair are scheming together again to find out Bart's secret. They discover that Lady Alexander was a horse, and Bart bought her and several other expensive horses from a man named Sheikh Hassan. Blair knows that there is a three-day horse show outside of town and maybe Sheikh Hassan himself or one of his horses will be there. Unfortunately, Chuck and Blair find out that Sheikh is dead, so they talk with his daughter Aman, who is very fond of Bart and won't say a word against him. But after Blair talks with her and convinces her that Bart is the bad guy and Chuck is not, Aman is confused. In the end of the episode, Chuck calls Blair and informs her that Bart was buying the expensive horses to cover up that he was really breaking a federal oil embargo. At the end of the call, Blair tells him that she was already planning their victory celebration in her head, and Chuck asks her to hold onto that thought.
In the episode Monstrous Ball, Chuck tries to get Lily on his side versus Bart, but doesn't succeed. Meanwhile, Dan attempts to woo Blair back by telling her that Chuck's battle with his father will never end, but she ignores him. When Blair finds out that Dan cheated on her with Serena, she slaps him, and he retaliates by saying that the ring around her neck will never be on her finger. She tells him she'd rather be with no one than with him, and then goes to see Chuck at his penthouse. She thanks Chuck for never sleeping with Serena, and he admits that even though she chose him, part of him always feared that Dan was the better man. She tells Chuck that no one is better for her than he is and that she will wait for him as long as it takes, and Chuck says that good things come to those who wait. They almost kiss but they are interrupted by Blair's phone. She kisses him on the cheek and leaves.
Chuck is about to get evidence about Bart's oil deals but Lily turns her back on him and burns the evidence. At the same time, Blair has a successful pop-up fashion show, fulfilling her side of the pact. She comes to see Chuck at the Empire to celebrate, but a devastated Chuck pushes her away, saying that they can't be together because he failed. Blair leaves crying. Afterwards, Chuck holes up in his suite, drunk and depressed, until a concerned Blair comes to snap him out of it. In a Thanksgiving dinner hosted by Serena and Dan, Chuck finally turns Lily against Bart and asks Blair to go to war with him. She happily accepts.
In The Revengers, Blair teams up with Sage, Ivy, Georgina, and Serena to take down Bart Bass. But Bart also threatens Blair's safety, forcing Chuck leave the city for Moscow and never come back. Chuck and Blair share an emotional farewell at the airport. Chuck gets on the plane and later that night at Bart's party it is revealed that the plane crashed and Chuck is presumed dead. Blair is devastated. However, Chuck arrives at the party and announces to the guests that his father tried to kill him. At the end of the episode, Chuck and Bart are having an argument on the roof and Chuck hits Bart in the face after he pushes him. Bart is about to attack Chuck, who dodges, and Bart falls over the edge of the roof. He hangs there asking for help, but Chuck refuses to assist him. Bart then falls to his death with only Chuck and Blair as witnesses. They run away from the scene while "to be continued" is flashed on the screen.
The final episode New York, I Love You XOXO begins where The Revengers ended. Fearful of the police, Chuck and Blair try to figure out how they can escape from the party. Blair calls to Georgina and asks her to look for Arthur, Chuck's limo driver. She finds him and Chuck and Blair hide in the car's trunk to avoid the police. Arthur drives them out of town to a hotel.
The next morning someone knocks on the door: Jack Bass, there to help. Jack tells them that he knew where they were because he has a tracking device in Chuck's limo. Jack asks if Chuck killed Bart, and he says he acted in self-defense. The only witness is Blair, since Bart had turned the roof cameras off. Blair says that she won't tell anyone that Chuck was on the roof with Bart. Jack says that there is another way to solve the situation: marriage. Jack tells them spousal privilege means that a wife cannot be forced to testify against her husband. At first Chuck opposes this plan, saying he doesn't want them to marry like this, but she reminds him that he was once afraid they would be boring together, and they clearly aren't that now. Chuck says that he was a stupid child when he said that and a life with Blair could never be boring. Chuck takes the ring from Blair's neck, gets down on one knee, and proposes. A happy and tearful Blair accepts.
Chuck and Blair go to the courthouse to get married, but he realizes that he doesn't want to start their life this way and that Blair should be married surrounded by the people she loves. Chuck calls their friends and family to come to Central Park and he and Blair announce, to everyone's surprise and delight, that they're getting married. But two little girls spot them and, frustrated by Gossip Girl not posting the tip, call the police instead. The wedding takes place in Bethesda Fountain in Central Park, with Chuck in a white tux and Blair in a gorgeous pale blue Ellie Saab gown. While Cyrus is reading their vows, everybody hears a distant police siren, and Blair asks if he can go a little faster; Chuck says that maybe they can skip to the I do part. The two get married and share a passionate kiss just as three police officers arrive and ask Chuck and Blair to come with them. Chuck and Blair are later released because the police have no evidence that Chuck was even was on the roof, and the only witness was Blair, now his wife. Bart's death will be ruled as an accident. Everybody gathers at the Waldorf's for a wedding reception. When everybody found out that Dan was Gossip Girl all along, Blair gets furious but Chuck calms her down. Dan tells them that Gossip Girl is dead and now they can really move on. Next we see them five years later, when Chuck and Blair are still happily married and have a son named Henry. Gossip Girl ends with Chuck and Blair holding hands as they watch Serena and Dan get married in their new house.
Chuck: Admit it. Even for me this is good.
Blair: If you weren’t such a perv, I am sure the CIA would hire you in a second.
Blair: I'm just saying, I have moves.
Chuck: Come on, you're ten times hotter than any of those girls.
Chuck: Not as clear as the memory of you purring in my ear which I have been replaying over and over.
Blair: Well erase the tape!
Blair: So do you...like me?
Chuck: Define like.
Blair: Ohh! Ahh! You have got to be kidding! I do not believe this!
Chuck: How do you think I feel? I haven't slept. I feel sick, like there's something in my stomach. Fluttering.
Chuck: Something this beautiful deserves to be seen on someone worthy of its beauty.
Chuck: You looked pretty hot on Prince Theadore's arm today.
Blair: Oh, is that what I am to you, just an accessory?
Chuck: Next to him, yes. On me, you'd be so much more.
Chuck: I was in love with Blair and I'm sorry.
Chuck: In the face of true love you don’t just give up – even if the object of your affection is begging you to.
Chuck: Let's take it slow this time. Do it right.
Blair: Chuck Bass is a romantic. Who knew?
Chuck: Well, now you do. That's all that matters.
Chuck: Look I should never have abandoned you. I know I made the wrong decision as soon as your plane took off. Distracted myself all summer...hoping I wouldn't feel it, but I still do.
Chuck: I was scared...I was scared that if we spent the whole summer together, just us, then you'd see.
Blair: See what?
Chuck: Me. Please don't leave with him.
Blair: Why? Give me a reason and "I'm Chuck Bass" doesn't count.
Chuck: 'Cause you don't want to.
Blair: Not good enough.
Chuck: 'Cause I don't want you to.
Blair: That's not enough.
Chuck: What else is there?
Blair: The true reason, I should stay right where I am and not get in the car. Three words. Eight letters. Say it...and I'm yours.
Chuck: We're inevitable, Waldorf. Blair: You mean Chuck?....What?
Serena: You smiled.
Blair: No I didn't! I hate Chuck, don't me lose my apetite!
Chuck: Say those three words you wanted me to say.
Blair: Are you kidding?
Chuck: Not quite. Eight letters. Three syllables. Say them and I'm yours.
Blair: I'm already yours, you're ruining the mood with all this talk.
Chuck: You can't say it. You wanted it from me.
Blair: I'm prepared to settle.
Chuck: Maybe I'm not.
Blair: Chuck Bass, I...will never say those words to you.
Chuck: Then you will never have me. I chased you for long enough, now it's time you chase me.
Chuck: The reason we can't say those three words to each other, isn't because they aren't true.
Emma: Was your first time with someone you love?
Blair: Yes. It was.
Blair: We both know that I'm your one and only. And a Canal Street knock-off seemed like the best option.
Chuck: My thinking exactly.
Chuck: Dance with me.
Blair: What's the point, Chuck. We're never going to be them. You said so, remember? It's not for us.
Chuck: Maybe. But I wouldn't change us. Not if it meant losing what we have.
Blair: And what do we have, Chuck? You tell me.
Chuck: Tonight. So shut up, and dance with me.
Blair: Chuck! Stop! Don't go. Or if you have to leave, let me come with you.
Chuck: I appreciate the concern.
Blair: No. You don't. You don't appreciate anything today. But I don't care. Whatever you're going through, I want to be there for you.
Chuck: We talked about this. You are not my girlfriend.
Blair: But I am me. And you are you. We're Chuck and Blair. Blair and Chuck. The worst thing you've ever done, the darkest thought you've ever had, I will stand by you through anything.
Chuck: And why would you do that?
Blair: Because I love you.
Chuck: I'm Chuck Bass! No one cares.
Blair: I do! Don't you understand? I'll always be here! I don't want you going anywhere. I couldn't bear it. So whatever you wanna do to yourself, please don't do that to me. Please.
Chuck: I'm sorry, I screwed up.
Blair: I believed in you. Your father believed in you. You...are the only one who didn't. All I wanted to do was...just, be there.
Chuck: This isn't you.
Blair: How do you know?
Chuck: Because I know you better than I know myself.
Blair: Last fall you said we couldn't be together, and I believed you. But everytime I try to move on, you're right there, acting like-
Chuck: Acting like what?
Blair: Like...maybe you want me to be as unhappy as you are.
Chuck: I would never wish that on anyone. I want you to be happy.
Blair: Then look down deep, into the soul I know you have, and tell me if what you feel for me is real, or if it's just a game. If it's real, we'll figure it out...all of us. But if it's not, then please Chuck, just let me go.
Chuck: It's just a game. I hate to lose. You're free to go.
Blair: Thank you.
Serena: Chuck, why did you just do that?
Chuck: Because I love her and I can't make her happy.
Blair: I know you told Serena you love me.
Chuck: Serena heard wrong.
Blair: Last year you told Nate, this year you told Serena. You tell everyone but me, why can't you tell me? You can't run, you have to stay here and here it this time. Chuck Bass, I love you. I love you so much it consumes me. I love you and I know you love me too. Tell me you love me and everything we've done, all the gossip and the lies and the hurt will have been for something. Tell me it was for something.
Chuck: Maybe it was, but it's not anymore.
Chuck: You were right. I was a coward running away again, but everywhere I went, you caught up with me. So I had to come back.
Blair: I want to believe you, but I can't. You hurt me too many times. Chuck: You can believe me this time.
Blair: Oh. That's it?
Chuck: I love you too.
Blair: But can you say it twice? No i'm serious, say it twice! Chuck: I love you. I love you. That's three. Here's four - I love you.
Blair: It's been three hours. I missed you
Blair: Summer was great. We had a lot of fun. Maybe summer's over. C huck: Okay, if that's what you want. Blair: Is that what you want?
Chuck: I want you to be happy. However that's achieved
Blair: What if we need games? What if without them we're boring?
Chuck: We can never be boring.
Blair: You say that, but I know you. You're Chuck Bass. C huck: I'm not Chuck Bass without you.
Blair: You okay? Chuck: I am now.
Chuck: I've been meeting with the board of Bass Industries all morning. I told them I wanna cash my shares out. Risk it all, on my own. They think I've lost my mind. Blair: Have you? Chuck: No.
Blair: Then how can you be so sure?
Chuck: Because you believe in me.
Chuck: I'm Chuck Bass. And I told you I love you. You're saying I'm easier to win over than a bunch of pseudo-intellectual homesick malcontents. You'd really insult me like this? Blair: That's not how it is. Chuck: That's exactly how it is. So the next time you forget you're Blair Waldorf, remember I'm Chuck Bass. And I love you.
Blair: Are you upset because you kissed a guy?
Chuck: I'm upset because it's somebody that wasn't you. You really think I've never kissed a guy before?
Blair: Love me?
Chuck: I thought you said you were going home? Blair: Changed my mind. Chuck: Well if i'd known, I would have come sooner. Did you ever find Brandeis? Blair: Yes. We're not friends anymore. But that's okay, I have you. That's all I need.
Chuck: Hey, do you mind if I stay?
Blair: Yes. But that's why I love you.
Chuck: My father always thought I was weak. And in the moment that mattered most I was. I couldn't be there when he...I left. Right away. I've been pushing myself to prove him wrong, and pushing you away. Blair: I don't think you ran away because you couldn't handle death. I think it's because you couldn't handle feelings. You're not like that anymore. You're strong. You carry people. You carry me. You're becoming a man in a way that your father never was.
Blair: Nothing is more important than being with you for this.
Blair: Your real mother would never turn her back on a chance to know you.
Chuck: I don't have a real mother Blair. I never will. B lair: That doesn't mean you're alone. I love you Chuck, and I'll always be your family.
Chuck: I love you. Saying it was hard, but I did and I've never looked back.
Blair: I've never thought it was possible to love someone too much, but maybe it is.
Chuck: No one could ever measure up to what we had.
Chuck: Excuse my confusion. I didn't expect to see you tonight.. or ever again. Blair: Sorry I was so late. Chuck: I waited. Blair: Dorota went into labor, she had her baby, I wasn't going to show up. I was resolved not to. Every bone in my body tried to slow me. Every voice in my head screamed "Don't!" Chuck: But..? Blair: But I didn't listen. I followed my heart because I love you. I can't deny that our path hasn't been complicated, but in the end love makes everything simple.
Blair: Just because you’re poorly dressed doesn’t mean you’re not Chuck Bass.
Chuck: Why would I want to be him?
Blair: You should have told me you were shot.
Chuck: I’m surprised you didn’t shoot me yourself.
Blair: I have. Many times, in my dreams. The good ones. But if you were really hurt, I would wanna know.
Chuck: When I woke up, my ID was gone. Nobody knew who I was, nobody was coming to look for me. I realised, I might be alive but Chuck Bass doesn’t have to be.
Blair: Changing your name doesn’t change who you are.
Chuck: It’s a good start. A chance to live simply, earn people’s respect. Maybe become a person someone could love.
Blair: Someone did love you. And you owe it to her and everyone else you’re leaving behind, not to run away. Which is what you’re doing. And I don’t think that great man you’re talking about wanting to be, is a coward. I think he would face up to what he did.
Chuck: I destroyed the only thing I ever loved.
Blair: I don’t love you anymore. But it takes more than even you to destroy a Blair Waldorf.
Chuck: Your world would be easier if I didn’t come back.
Blair: That’s true. But it wouldn’t be my world without you in it.
Chuck: Blair, just listen to me.
Blair: Why did you do it? Because I knew that Jack was in Chile last summer? I only found out because I was desperate for news of you.
Chuck: You were?
Blair: All summer. When I was pretending not to care. I wanted to know where you were. I paid a private eye to look, but the only Bass he got was your scaly uncle.
Blair: My black Balenciaga will be perfect to publicly condemn you.
Chuck: I love poplin.
Blair: I love condemnation.
Chuck: I love you.
Blair: [pause] Of course no one does black like Dior.
Chuck: I appreciate you being here in that dress, but don’t you have a denouncement to attend?
Blair: Dorota is distracting them. I heard what you said.
Chuck: What conversation are you referring to exactly?
Blair: Three one syllable words that under the circumstances you may or may not have meant.
Chuck: Do you want me to have meant them?
Blair: If they were true, I would wanna know. Of course, people do lose their rational thought during sex. They bark and scream out for God and their mothers. I should get back to Anne.
Chuck: I meant it Blair. With all my heart. Are you gonna say something this time?
Blair: I will, I mean I do.
Chuck: You realize we can’t have everything. Anne won’t be the only person who might think you’re weak for forgiving me.
Blair: And you won’t build up a business based on being New York’s bad boy bachelor.
Chuck: I understand the consequences. Are we willing to pay them? [Curtain falls down]
Chuck: I say we go up in flames together.
Chuck: I’ll give you the money to start whatever foundation you want.
Blair: It won’t change anything. Anne’s right. As long as I’m with you, I’m Hilary in the White House. And I want to be Hilary, secretary of state, but with better hair.
Chuck: Then you’ll find another way to show the world that you’re a force to be reckoned with. We can build our futures together.
Blair: I followed my heart all last year and it led me nowhere. Now I need to follow my head.
Chuck: You don’t need to choose between them. Look at Brad and Angelina. They take turns on top!
Blair: Yeah, but she won an Oscar first. I’m sorry but I have to be Blair Waldorf before I can be Chuck Bass’ girlfriend.
Chuck: I love you.
Blair: I love you too. I don’t expect you to wait.
Chuck: Two people that are meant to be together, eventually they’ll find their way back.
Blair: Do you really believe that?
Chuck: I do.
Blair: So do I.
Blair:[in her note to Chuck] Just because we can’t be friends doesn’t mean we aren’t.
Chuck: It’s no surprise she went for a prince. Marie-Antoinette was one of her favorite roles to play. Of course I was always eating her cake.
Princess Sophie: How dare you? And you are?
Chuck: I’m Chuck Bass, the love of her life. Anyone else is just a waste of time.
Chuck: You came.
Blair: How could you do that to me, Chuck?
Chuck: I’m sorry I ruined your shot at being a princess. Let’s face it, you were never gonna go through with it.
Chuck: I need you Blair. Like I never have before. Everything I believed about my father, everything I thought I wanted to be, I needed to be for him. It was all based on lies. The only thing that has ever been real is me and you. You know that. That’s why you came back to me.
Blair: Louis asked me to marry him.
Chuck: Never marry anyone else, you’re mine.
Blair: I wanted to be. I wanted it so badly but.. not anymore.
Chuck: You’re mine Blair!
Blair: Stop it Chuck! I said it’s over.
Chuck: No!'thumb|260px|link=File:Tumblr_m6wwwhzZ391qd2k1no1_500.gifChuck: Hello?
Blair: I don’t understand why you’re doing this. You tricked me into coming to Chuck’s new hotel by saying that he was in jeopardy and now you won’t let me leave. What am I supposed to do, jump from a third story window? Chuck: Come on. I know where Blair is. Smart girl. Russell: You and Chuck might not be together right now Ms. Waldorf, but from what I can tell, you’re still the thing he loves most in the world. You’re not going anywhere tonight.
Chuck: You really love him, don’t you?
Blair: Yes. But not like I love you. Louis and I, it’s different. It’s lighter, more simple. He makes me happy.
Chuck: And I don’t?
Blair: What we have is a great love. It’s complicated. Intense. All-consuming. No matter what we do and how much we fight, it’ll always pull us in. What’s mere happiness in the face of all that, right?
Blair: Why did you just do that?
Chuck: Because of what you said earlier.
Blair: About being happy? Chuck, that’s not the most important thing. People don’t write sonnets about being compatible. Or novels about shared life goals and stimulating conversation. The great loves are the crazy ones. L’amour fou.
Chuck: Blair we’re not living in Paris in the 20s.
Blair: Well we both wish we were.
Chuck: There’s a difference between a great love and the right love. I left the Empire State Building last year after two minutes when you didn’t show. Louis waited all night. This is your chance at happiness. You think you shouldn’t want it ’cause you’ve never had it and it scares you. But you deserve your fairytale.
Blair: We make our own fairytales.
Chuck: Only when we have to. You don’t. How do you feel about tonight?
Blair: Awful. I just.. terrible. In fact I’ve never felt like this before.
Chuck: Guilt. I feel it too. Maybe I’m actually growing up after all.
Blair: I didn’t want to let you go just yet.
Chuck: Don’t let anyone tell you you’re not powerful. You’re the most powerful woman I know.
Blair: It’s taking all the power to have to walk away from you.
Chuck: I know. But I need to let you go. You need to let go.
Blair: I will always love you.
Chuck: I will always love you.
Blair: I need to talk to you.
Chuck: I thought we said everything we needed to say last time we saw each other.
Chuck: If this is another misguided attempt by Dan to make me feel something.
Blair: I’m pregnant. It’s Louis’. I didn't want you to find out from someone else and wonder if the baby was yours.
Chuck: That’s very considerate.
Blair: Yes. Well. If I know anything about Chuck Bass, it’s that fatherhood isn't part of the lifestyle.
Chuck: You must have very been relieved when you realized you weren't carrying my offspring.That certainly would have derailed your fairytale.
Blair: This fairytale is complicated.Chuck:Blair.Meet my dog, Monkey.Blair:I saw Gossip Girl. I thought you got rid of him.
Chuck: I just had him to get fixed. I thought it was the responsible thing to do.
Blair: I should go.
Blair: Louis is waiting for me.
Chuck: Of course.
Blair: There is a part of me that really wanted it to be yours.Chuck: I’m not here to apologize about what happened tonight.
Blair: Then what are you here to apologize for?
Chuck: Everything else. I’m sorry for losing my temper the night you told me Louis proposed to you. I’m sorry for not waiting longer at the Empire State Building. I’m sorry for treating you like property. I’m sorry I didn’t tell you I loved you when I knew I did. Most of all I’m sorry that I gave up on us when you never did.
Blair: Thank you. I hope never giving up on people isn’t going to be my downfall.
Chuck: That’s why you’re going to be an amazing mother. You’re always there for the people you love. Even when they don’t deserve it.
Blair: You know that’s never going to change.
Blair: All this time I’ve blamed you. For pulling me into the dark. But I was wrong. It was me who brought out your dark side. And now that I’m with Louis I’ve done the same to him. I’m sorry.Chuck: You never pulled me to the dark side, Blair. Blair: I appreciate you trying to make me feel better, but I have my answer. Chuck: You’re the lightest thing that ever came into my life. Blair: Then why did it take letting me go to find this whole new side of yourself? Chuck: I only turned dark and desperate because I was afraid of losing you. Your love kept me alive. Blair: But you survived without me. Chuck: The worst thing happened and I didn’t die. But I had to find a way to move on with my life. I only want you to be happy, I’m just sorry it couldn’t be with me.
Nate:You still love her, huh?
Chuck:I can't imagine the day I won't.
Blair: What’s going on? Do you have something to do with this?
Chuck: No. Dan arranged it for us.
Blair: What us?
Chuck: The us I should have fought for when you called.
The us that is not just you and me, but you, me and your baby.
Blair: Then why did you tell me to choose Louis?
Chuck: I thought it was selfish if I was the one to tell you to break up your family.
Blair: That was the moment you chose not to be selfish?
Chuck: Timing has never been our strong suit. I had it all wrong. Just because Louis is the father of your baby does not mean you should be with him, you should be with me.
Chuck: Because I’m going to love your baby as much as I love you.
Blair: I have to tell Louis face to face that the wedding is off, he deserves at least that.
Chuck: Are you sure you wanna do this? I mean a prince, a fairytale wedding, that’s all you ever wanted.
Blair: You’re all I ever wanted. I love you. I love every part of you. I coulnd’t tell Louis that he would never lose me because it wasn’t true. You’re the one I never want to leave.
Blair: Just because we can’t be together, doesn’t mean I won’t love you.
Chuck: Don’t marry him.
Blair: All those people out there are waiting for me.
Chuck: Yes they are. But they also want you to be happy, which you’re not going to be if you go through with this. Tell me I’m wrong and I’ll leave. You can’t. Because it should be us up there and you know it.
Blair: It isn’t that simple.
Chuck: It’s only that simple. You told me you loved me. I know it was true.
Blair: It is! Of course I love you, Chuck. I’ve always loved you. I love you more and more every day if it’s even possible to love someone that much.
Chuck: Get out of here with me right now. We can go anywhere just as long as we’re together.
Blair: I know you can’t understand, and I don’t expect you to, but even if I weren’t with Louis… I couldn’t be with you. Just know that not living with you is the hardest thing I’ve ever done. But at least I have someone who loves me by my side. You should find someone who loves you too.
Chuck: I have. She’s standing right in front of me.
Blair: I know it sounds crazy, but I really am doing this for you.
Chuck:I can’t stand the thought of you with anyone else. I don’t care what it costs or where we have to go. I just want to be with you.Chuck: After everything we’ve been through, there is no room for secrets. Nor should there be. Whatever it is, you can tell me, Blair. It’s just us here, you and me
Chuck: I don't need your pity.
Blair: I'm not here because I pity you.I'm here because it's time I was honest with you. I love you. I'm in love with you. I have tried to kill it, to run away from it, but i can't. And I don't want to anymore.
Chuck: So what?
Blair: So now we can be together. Isn't that what you want?
Chuck: It was. Before I lost everything.
Blair: Bass indutries isn't everything. I'm going to take over my mother's company and that can be our future.
Chuck: The only reason Waldorf Designs has a future is because I gave mine up for it. My father was right. I always put your first. And you bet against me every time. And now I have nothing.
Blair: You have me.
Chuck: That's not enough. I need a future.
Blair: Then let me be a part of it.
Chuck: I don't want to be Mr. Blair Waldorf. I'm Chuck Bass.
Blair: You fought for me all year, I've come to fight for you. You said I always bet against you, but this time I'm all in.
Blair:The two of us alone in your limo.Very tempting fate you know that? Maybe our pact is just an excuse for us not to be together.
Chuck: Blair, I love you with all my heart and that is the reason I cannot take the chance of messing this up.It wont be much longer I promise
Chuck: Blair you are a distraction because when we're together you're all I think about. And I would give up my empire for you. I would give up everything for you.
Blair: Just because we can't live happily ever after doesn't mean we can't have a little fun once in a while.
Chuck: We made a pact. Need I remind you what that means?
Blair: But it's been too long since Monaco and Pocahontas needs her John Smith.
Chuck: I always thought of myself as a John Rolfe kind of man.
Blair: That's my Chuck. You can play both after dinner.
Chuck: And you're sure Lily and Bart are gone?
Blair: They are and now so is my appetite. When was the last time you showered?
Chuck: Only if you join me.
Blair: Chuck, stop! What are you doing?
Chuck: I couldn't live with myself if anything happened to you.
Blair: But I'm fine.
Chuck: Because I'm leaving. It's a small price to pay for your safety.
Blair: But I don't wanna be safe. I want to be with you. Come on, lets go together. I'll have Dorota send my things.
Chuck: Blair, I can't. I have to go alone. I made a deal. Those were my father's terms. Just have faith,in me this one last time.
Blair: But I waited too long. I need to be with you now.
Chuck: Blair trust me, letting me go is the right thing to do.
Blair: Don't get on the plane. Bart has already hurt so many people.
Chuck: I know what my father is capable of, but he would never try to kill his own son.
Blair: Then do one thing before you go. Kiss me, Chuck Bass.
Chuck:Life with you could never be boring.Blair Cornelia Waldorf will you marry me ?
Blair:Yes!Yes I will.
Cyrus: Do you, Chuck, take Blair to be your lawfully wedded wife?
Chuck: Three words, eight letters.
Cyrus: Blair, do you take Chuck to be your lawfully wedded husband?
Blair: One word, three letters. Yes.
- They are the most popular couple of gossip girl.
- Chuck and Blair's relationship didn't last in the books.
- In the book Chuck was completely in love with Blair but Blair wanted to experience life so she went travelling the world with Serena after she broke up with Chuck.
- They won the hollywood life poll for the hottest tv couples.1
- They won the hollywood life 25 hottest tv couples tournament 2012.2
- They came 5th in the top 10 couples of 2007-2008.3
- They came 1st in the top 10 couples of 2008-2009.4
- They came 1st in the top 10 couples of 2009-2010.5
- They came 4th in the top 10 couples of 2010-2011.6
- They came 1st in the top 10 couples of 2011-2012.7
- They came 1st in the top 10 couples of 2012-2013.8
- Won the wetpaint poll of the sexiest couple on scripted tv.9
- Won the hollywood life poll for the tv couples we want to see together in 2012.10
- Won EW's sexiest couple on network tv poll.11
- Won the poll for the best tv romance of 2009.12
- Won the poll for the best tv romance of 2010.13