"So the next time you forget you're Blair Waldorf, remember I'm Chuck Bass, and I love you."
-Chuck to Blair, Dan de Fleurette
Blair and Chuck grew up together on the Upper East Side, along with their respective best friends Serena van der Woodsen and Nate Archibald. Blair loses her virginity to Chuck in Victor Victrola, and they officially enter into a relationship in The Goodbye Gossip Girl.
After the events in Inglourious Bassterds, Chuck and Blair ultimately split up in The Unblairable Lightness of Being. Throughout seasons four and five, the two go back and forth with their relationship. In the season five finale The Return of the Ring, Blair chooses to be with Chuck and they make a pact to ensure they end up together. In the series finale New York, I Love You XOXO, the two get married. In the time jump, they have bought a townhouse in the city together and have a son, Henry Bass.
Blair and Chuck have no real relationship other than acquaintances; as Chuck is a minor character in the books. The two date in London for a year, but break up.
In Pilot, Chuck and Blair appear to have an acquaintance-like friendship. 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. Shortly after, in The Wild Brunch, Chuck's father Bart Bass hosts his annual brunch for his foundation and Blair and Chuck sit together; along with Nate, Isabel Coates, and Kati Farkas. 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 vents to Chuck, who offers to help by giving her the key to his suite to finally have sex with Nate. Later, they both take part in informing Dan about Serena's indiscretions with Nate. In Poison Ivy, the junior class of Constance Billard/St. Jude's throws a mixer for representatives of Ivy League colleges. After her fight with Serena turns physical, Blair calls Chuck for help in getting revenge. She explains that she needs answers on why she returned to New York, and Chuck is willing to help her get them. He follows Serena and sees her entering The Ostroff Center, a rehab facility where, unknown to Chuck and Blair, her brother Eric van der Woodsen is staying. Chuck takes photos and shows them to Blair, who is pleased with what he found. She uses the information to out Serena as a drug addict during the mixer, but later learns it was Eric who was there.
In Victor Victrola, Chuck invites Blair to come see the club he's trying to convince Bart to buy, and she's impressed with the place. However, Bart doesn't like the place and shames Chuck for looking for more ways to be around strippers and parties. Meanwhile, Blair learns from Jenny Humphrey that Nate mistook her for Serena and confessed that he still has feelings for her. As a result, she breaks up with him and heads to the club, Victrola, to escape her troubles with Chuck. While there, Chuck dares her to get onstage and she surprises him by going up and dancing. At the end of the night, he takes Blair home in his limo and she ends up losing her virginity to him in the backseat.On her seventeenth birthday, Blair realizes how much she misses Nate and wants him back. To remind herself of this, she disinvites Chuck from her birthday party before going to the jewelry store to pick out gifts for others to pick up. Meanwhile, Nate's mother Anne Archibald tries to convince him to get back together with Blair to secure Eleanor's support in their recent legal battles regarding Howard Archibald's embezzlement. Feeling pressured, Nate confesses what his mother wants him to do to Chuck, who uses that information to ruin Blair's interest in winning him back. Blair is unconvinced, and promises Chuck that Nate will call her at midnight the same he does every year on her birthday. Unfortunately, he doesn't call and Blair instead gets a Gossip Girl blast containing a picture of Nate and a blonde, who is unnamed but Jenny. She excuses herself from her party crying, and says her birthday wish didn't come true. Chuck follows her, and gives her the diamond necklace she put on hold earlier that day. The two begin to kiss, and Serena sees them together (Seventeen Candles).
Cotillion season arrives, and it's revealed that Chuck and Blair still hook up from time to time. However, Blair is planning to attend The Debutante Ball with Prince Henry and Chuck will be escorting someone else. Meanwhile, Nate is noticing Blair's newfound happiness and realizes he misses her. He shows up to her penthouse after dance rehearsal one evening and asks her to go to the ball with him instead. She agrees while a jealous Chuck listens from upstairs. He tries to get Nate to lose interest in Blair by dropping hints that she's interested in his enemy Carter Baizen. On the night of the ball, Chuck goes to see Blair but she orders him to leave her and Nate alone for the night; and she accidentally reveals that Carter is on his way over to retrieve a jacket he left during tea. Chuck waits around for him, and takes a picture of him leaving the building to show Nate to prove he's dating Blair. Nate falls for it, and punches Carter at the ball, getting himself kicked out over it. Later while dancing, Blair realizes Chuck set Carter up to make Nate jealous and was ultimately responsible for the scene. She ends their affair, and goes to find Nate. Afterwards, he sees them enter a room together kissing and broken hearted, he leaves the city (Hi, Society). Before Christmas, Blair, newly reunited with Nate, tries unsuccessfully to contact Chuck to ask him to keep their affair private. On Christmas morning, he texts her a photo of himself with Nate, asking her who he would want to tell (Roman Holiday).When Chuck returns, he continues to remain jealous of Blair and Chuck, and tells her not to do anything with Nate or he'll reveal what they did. As a result, Blair distances herself from Nate, despite his attempts to bring them closer together. After an incident at the school swimming pool, resulting in everyone getting in trouble, Nate finds the key to the pool in Blair's room and turns himself in as the false culprit to save her from getting in trouble. Meanwhile, Dan's best friend Vanessa Abrams catches Blair and Chuck fighting about their affair on videotape, to the horror of both of them. Chuck buys the tape for ten thousand dollars, but she gives him a blank one while she gives the real one to Blair (School Lies). In A Thin Line Between Chuck and Nate, Blair has a pregnancy scare and isn't sure whether Chuck or Nate could be the father. She takes a test and finds she isn't pregnant, and tells Chuck that she chooses to be with Nate. Hurt, Chuck tips off Gossip Girl that Blair slept with two guys in one week. When Nate finds out and doesn't believe the rumor, Jenny confirms it for him and he gets into a fight with Chuck. He also breaks up with Blair. Feeling alone, Blair goes to see Chuck and tells him he is all she has now. However, he tells her that he is no longer interested in her and wants nothing to do with her.
In Desperately Seeking Serena, Serena's old frenemy Georgina Sparks returns to the UES and stirs up trouble for her. After reminding her of their past, Serena has a breakdown in front of Blair, Chuck, and Nate. Wanting to help, the three team up to help her find closure and take down Georgina (Woman on the Verge).On the eve of Bart and Serena's mother Lily van der Woodsen's wedding, Blair and Chuck spend the night together to find the perfect plan to get rid of Georgina.In the season finale Much 'I Do' About Nothing, they wake up together, and Chuck goes to prepare his best man speech while Blair is to carry out their plan. At the wedding, Chuck dedicates his speech to Blair and announces he intends to fight for her. Afterwards, they dance together and agree to take their relationship slow. A week after the wedding, Blair is packing to spend the summer in Europe with Chuck. However, Chuck is beginning to have doubts about his ability to commit and becoming fearful of growing up, backs out of going on the trip to sleep with Bart and Lily's apartment decorator. His choice leaves Blair waiting for him on the helipad, before choosing to fly to Tuscany without him.
In the season premiere Summer Kind of Wonderful, it's revealed that Chuck never made it to Europe and left Blair hanging all summer. He instead went to the Hamptons with Serena, Eric, and CeCe Rhodes, sleeping with a different girl every night to get over Blair. When she returns, she brings along her new boyfriend Marcus Beaton, much to Chuck's dismay. He becomes suspicious of Marcus, especially after hearing him say things about his life that doesn't match with what he told Blair. During the annual Vitamin Water White Party, Marcus reveals to Blair that he is a British Lord that lied about his identity to make sure she wasn't using him. At the end of the party, Chuck approaches Blair while she is waiting for Marcus and asks her not to leave with him. She asks him to admit he loves her and she'll leave Marcus to be with him, but he is unable to do so. Hurt, Blair leaves with Marcus. After returning to Manhattan, Blair throws a spontaneous back to school party to impress Marcus' step-mother, Duchess Catherine Beaton. Wanting to ruin her chances with Marcus, Chuck sets Blair up to insult Catherine before she officially meets her. However, his plan doesn't work out when Blair catches Catherine with Nate and is able to blackmail her into giving her approval (Never Been Marcused). Soon after, Chuck begins to have intimacy problems, which Serena diagnoses with having to do with his inability to move on from Blair. At a party she's throwing, he asks her to sleep with him but she refuses. Later during the party, the whole city experiences a blackout and Chuck feigns as Marcus to get Blair to kiss him and hopefully have sex with him. She falls for it, and Marcus walks in on them kissing. At first Blair says she didn't know it was Chuck, but later admits she knew it was him. However, Marcus forgives her and Chuck continues to experience intimacy problems with other women (The Dark Night). Meanwhile, Vanessa has taken an interest in Nate, which she loses when she learns he's sleeping with Catherine for money. She soon discovers that Catherine is also sleeping with Marcus, and she tells Blair hoping to get Nate out of the arrangement. As a result, Blair ends things with Marcus (The Ex-Files). Later, Vanessa uses the pictures she took of Marcus and Catherine to blackmail Blair into helping her save an old Brooklyn bar. Angry at being played, she entices Chuck into seducing Vanessa for humiliation, promising to sleep with him if he succeeds. He agrees, but finds he likes the bar and plans to actually save it. When Blair realizes he is acting friendly with Vanessa and planning to help her, she ends the game and announces to him that he won after telling Vanessa everything. When he comes to collect his prize, a night with her, he asks her to say she loves him. She refuses, saying she will never say those words to him and he replies that it's now her turn to chase him (Chuck In Real Life). After this incident, Blair becomes obsessed with getting Chuck to sleep with her. Serena suggests she ask Dan for help, and he advises that she become unavoidable to Chuck to make sure she's in his head. Following his advice, she asks him out for drinks but he catches on to her desperation pretty quick and leaves when she spills her drink on his pants. After she explains what happened to Dan, he suggests she catch him at home. She goes to the VDW's and succeeds in getting him to kiss her, but their foreplay is interrupted when a text from Serena reveals her plans. In a last ditch attempt, Blair decides to just tell him how she feels at Rufus Humphrey's art gallery opening. Before she goes through with it, Dan finds out what she and Chuck did to Vanessa so he instills doubt in her telling him. As a result, she fails in doing so and Chuck, annoyed with her games, ends their relationship for good. However, Dan tells Chuck that he ruined Blair's revelation and was the result of the failure. Later that night, Chuck goes to see Blair and tells her that despite their mutual attraction to each other, they aren't ready for a relationship. They agree that they love the game too much to stop, and they decide to put their relationship on hold (Pret-a-Poor-J). While babysitting a prominent Yale donor's daughter named Emma, Blair and Chuck end up on a wild goose chase to find her after she runs away, determined to lose her virginity. They eventually find her at a hotel with a boy from her school nicknamed "The Devirginator", but Chuck has Gossip Girl send out a fake blast about Emma's enemy Muffy losing hers first. Disappointed, she goes home with Blair, who recognizes parts of herself in Emma. She asks Blair if she lost her virginity to someone she loves, and Blair says yes (There Might be Blood).Before the annual Snowflake Ball, Chuck and Blair make a bet to bring dates for the other to prove how well they know each other. If Blair likes her date, she gets Chuck's limo for a month and if Chuck likes his date, he gets Dorota. Blair enlists Dorota to help her find him a date, and Dorota notices the girl that is being described is exactly like Blair. At the ball, Chuck and Blair both show up with the dates and discover they brought similar versions of themselves. When they go off the argue, their dates hook up, leading Blair to express frustration that even their dopplegangers can work out their issues but they can't. Chuck tells her that even though they can't be them, he doesn't want to lose what they have. The two dance before Chuck receives the news that Bart died in a car crash (It's a Wonderful Lie).<p>After learning his father has died, Chuck goes into hiding at The Palace Hotel from everyone, including Blair. At the funeral, Blair works to make sure Chuck behaves and appears sober, despite finding him completely wasted beforehand. During the reception, Nate tells her how she's being sweet and maternal toward him, but she denies it. When he leaves, Blair chases him down and finally tells him that she will stand by him through anything because she loves him. Overwhelmed by grief and alcohol, Chuck blows her off and leaves anyway, leaving Blair crying on the street. The next night, Eleanor Waldorf and Cyrus Rose get married at the Waldorf's, and Chuck arrives during to go to Blair's room. Dorota tells her, and Blair heads up to find Chuck sitting and crying on her bed. She hugs him, and they spend the night cuddling together. When Blair wakes up in the middle of the night, she finds a note from Chuck saying she deserves much better and not to come looking for him (O Brother, Where Bart Thou?). Chuck eventually returns to Manhattan with his uncle Jack Bass. When Blair hears he's back, she goes to see him but leaves quickly once she sees his disheveled state. However, she still tries to support him; including acting as his representative at a meeting with Headmistress Queller after she catches him smoking hash at school. He throws a party at Victrola, and ends up on the roof, drunk. Blair finds him up there and is able to talk him down, promising that she doesn't want him going anywhere and cares about him. When she and Jack bring him home, she tells Jack not to tell Chuck what they did on New Year's Eve (In the Realm of the Basses)<p>When Bart's will is read, Blair and Nate go along for support. Afterwards, they all learn that Chuck was left the majority shares of Bass Industries, much to Jack's dismay. At first, Chuck decides he doesn't want it but after reading a letter from Bart, he decides to take a shot at it. Jealous at not getting the company, Jack convinces Blair to help him throw a surprise brunch for Chuck to show their support. She initially agrees and plans a huge party at The Palace. However, Jack arranges for Chuck to be caught by the board of Bass Industries while he's high on cocaine and seducing prostitutes upstairs. As a result, they vote to take him away from the company and an angry Chuck takes it out on Blair; ordering her to stop pretending to be his wife. After he calms down, he goes to see her at her penthouse and brings her flowers as an apology. She doesn't accept it, and tells him she's done (Gone with the Will).
Soon after, Blair is officially rejected from her dream school, Yale University, so she goes in search of a wilder lifestyle: which includes Chuck's enemy, Carter Baizen. During a party thrown by Nate's family, Chuck and Serena attempt to find Blair to change her back to who she was before. When Chuck finally corners her, she refuses to change back to who she was and tries to proposition him into having sex with her. He refuses, claiming it isn't the Blair he wants, so she leaves him. Later that day, Nate sits down with her and they have a deep talk about not fighting against who you are. That night, Chuck goes to the Waldorf's to talk to her, but finds Nate's jacket and realizes he's upstairs with Blair (The Grandfather). They become closer again, which makes Chuck jealous. He tries to tell Blair that she never had any sparks with Nate, and reminds her that there's a reason he won't break up with Vanessa. Trying to prove Chuck wrong, she attempts to get Nate to break up with Vanessa to be with her; which he eventually does. However, a still jealous Chuck finds Vanessa after the break up and tells her that Nate left her for Blair. Angry, they try to come up with a way to get back at them. After seeing them together at Jenny's Sweet Sixteen party, they kiss. Both Blair and Nate see, but it doesn't bother them too much as they get back together officially the next day while Chuck has sex with Vanessa (Remains of the J).
Meanwhile, Serena has begun dating Gabriel Edwards, a former boyfriend of her friend Poppy Lifton. However, Blair is suspicious of him and becomes even more so when Serena tells her that Gabriel has a tendency to disappear at times, isn't easy to make plans with, and that he supposedly met Serena while she was impaired with Georgina at a restaurant Blair closed down herself to use for a scheme. On one occasion, she waits outside Serena's building to see where he'll disappear to and Chuck sees her spying together. They see him meet up and kiss Poppy, and together they decide to expose him. When Nate finds out they were together, he buys an apartment to live in with Blair while they go to different schools. He also tells Chuck to stay away from Blair unless he's going to tell her how he feels because he wants her for himself. During a gathering at the VDW's, Chuck tracks down Georgina Sparks, the only one who would know what really happened the night Gabriel met Serena. When Nate finds out Chuck wants Blair to go with him to talk to Georgina, he asks Blair to stay with them in their new apartment but she chooses to go with Chuck. However, after the two fall asleep together all night in his limo waiting for visiting hours, she realizes he only brought her to keep her away from Nate. As a result, she takes his limo when he goes to find Georgina to go and see Nate (Southern Gentlemen Prefer Blondes).
On his way back into the city, Chuck learns that Serena has found out that Gabriel is indeed lying to her about meeting her and she doesn't know what else he's lying about. Together with Blair and Nate, they corner Gabriel into confessing that Poppy is pulling all the strings and is taking money from their faux fundraiser for herself. They set up Georgina to meet with Poppy to catch her in the middle of conning but and while this is being carried out, Blair asks Chuck if what they have is real or if he's just playing a game with her. Fearful of not being able to make her happy, Chuck lies that he's just messing with her and Blair leaves crying (The Wrath of Con). The next day, Nate finds out that he is unable to get a limo for prom, that he can't get a corsage, his hotel plans were ruined, and Blair's dress was destroyed at the dry cleaners. He asks Chuck if he had anything to do with the sabotage, but he denies it. Meanwhile, Blair receives her dream dress from Paris to wear, and Chuck gives Serena the key to the penthouse at The Plaza Hotel to give to Blair: both things Blair planned out in her prom scrapbook as a child. At prom, Penelope, Hazel, Isabel, and Nelly plot to humiliate Blair by rigging the prom queen election to make Nelly win but are shocked when Blair is announced the winner. Privately, Chuck reveals that he voted for Blair about 150 times and removed all the ballots for Nelly from the box so she could have the prom of her dreams. At the end of the night, Blair and Nate break up due to feeling like they've outgrown their relationship (Valley Girls).
In the season finale The Goodbye Gossip Girl, Serena tries to encourage Blair to tell Chuck how she feels, but Blair is unable to; especially after Gossip Girl labels her as weak. At Nate's graduation party that night, they end up in a room alone together and are about to admit their feelings when a Gossip Girl blast reveals that Chuck slept with Vanessa and Blair slept with Jack on New Year's. As a result, Chuck loses any interest in being with Blair, even though she tells him she loves him. A week later, Blair tells Serena that she is planning to have a quiet summer and she knows that Chuck has been in Europe. Later that day, Blair is walking home when she sees Chuck waiting for her on the street. He explains that while he was in Europe he couldn't get her out of his head and brought her her favorite things to make things right. Finally, he admits that he loves her too and they kiss; entering into a relationship.Reversals of Fortune, it's revealed Blair and Chuck have been in a relationship all summer but to keep the excitement in place, they play a game that involves Chuck flirting with other women and Blair "catching" him before humiliating the woman. However, Serena and Nate are skeptical of the game and encourage the two to make sure both totally enjoy it and aren't just doing it to please the other. After Blair becomes jealous and mistakenly thinks Chuck really cheated on her, they end their game to move onto a new stage in their relationship.In The Lost Boy, Chuck purchases The Empire Hotel and tells Blair that he wanted to take such a big risk because she truly believes in him. Soon after, he becomes immersed in his work and Blair continues to struggled at NYU. After she decides to skip a movie premiere her whole dorm was invited to, he invites Jenny to go with him in her place. When she finds out, she tracks them down and begins to lay into Jenny until Chuck admits it was all his plan. He tells her that she is special and will achieve what she wants in due time. After they talk, she is stopped by a paparazzo who asks to take her photo. It's later revealed Chuck paid the photographer to take the photos as a way to help Blair feel special and give her some confidence (Dan de Fleurette). Not too long after, Blair fights with Vanessa about who gets to give the Freshman Toast at Parent's Weekend. As a way to win, she makes a deal with NYU alum Josh Ellis to let him kiss Chuck if she can give the toast. She convinces Chuck to play one last round of their game from the summer and he ends up kissing Josh. As a result, she gets the toast and Chuck goes off to a meeting. However, it's cancelled and he arrives at the Freshman Dinner in time to hear her unknowingly announce to everyone that she had no remorse for using Chuck to get what she wanted. When she learns he found out, she tries to apologize but he tells her he needs some more time to think about things (Enough About Eve). On Halloween, Chuck takes Blair's suggestion to open his hotel club but tells Serena, who is newly employed with a publicist, to not let her anywhere near the plans. Blair, who is with Serena when Chuck makes the request over the phone, is hurt and calls Jack to expedite Chuck's liquor license as a way to help. However when Chuck finds out what she did, he bans her from the opening for betraying him. The night of, she receives flowers from Jack and realizes he had a fake license made and is going to use it against Chuck. She goes to the club to warn Chuck but finds he had already figured out it was a fake, and they plot together to call the cops and squeeze all the publicity they can out of being shut down. Afterwards, they make up and agree to try and trust each other more (How to Succeed in Bassness).On the one year anniversary of Bart's death, Blair tries to be around Chuck as much as possible in case he may need her but he pushes her away. When Serena gets into a car accident with Nate's cousin Tripp van der Bilt and ends up in the hospital, both Blair and Chuck go to see her. While at the hospital, Chuck begins to have flashbacks to when Bart was dying in the hospital after his accident. Blair sits with him and comforts him, and they go together to the cemetery for him to properly mourn his father's death. When they're there, Chuck gets out of the limo to bring flowers to the grave but finds a woman crying over the headstone but she runs off before Chuck can say anything to her. When she's gone, Chuck finds half a locket lying on the ground with a photo of Bart inside (The Debarted). Afterwards, he tells Blair he has no interest in the locket or who it belongs to but she later finds out that despite this, he has been looking into it. At the same time, he promises to introduce her to a supposed member of La Table Élitaire named Henri Duris but continually cancels on her to track down the woman, who is named Elizabeth Fisher. After looking through all the evidence, he finally realizes that she is his mother and Blair goes with him to confront her. They do, and she denies being his mother. Devastated, he decides to stop looking and Blair continues to support him (The Hurt Locket). However in The Lady Vanished, she comes forward and admits that she is his mother. They begin to build a relationship until Jack has some women leverage lawsuits against Chuck for sexual harassment. To save the hotel from failing, he signs the hotel over to Elizabeth but finds out that she was working with Jack and his lawyer to steal it from him (The Empire Strikes Jack).In Inglourious Bassterds, Jack tells Chuck if he wants the hotel back he can have it: in exchange for a night with Blair. Later, Jack runs into Blair and says that his price for the hotel is a night with her but Chuck never considered it. However, after Jack sends her a dress saying she has one last chance to save Chuck and seeing how crushed Chuck is from losing his hotel, she goes to Jack willingly; but brings a contract to sign to make sure Chuck never finds out and that he holds up his end of the deal. Instead of doing anything with her, he tells her how everything was set up by Chuck because he knowingly sold her out for his hotel by preying on her compassion and need to help. She goes home to find Chuck in the lobby of her building and they fight over what just happened. He tells her that even if he set her up, no one forced her to go see Jack and she slaps him before going upstairs alone. Afterwards, in The Unblairable Lightness of Being, Chuck finds out that Blair's maid, Dorota Kishlovsky is in a bind and needs to get married to her fiancée, Vanya, before her parents arrive and find her unmarried and pregnant. After being encouraged by Serena to do a grand gesture for Blair to get her to forgive him, he decides to throw them a traditional Polish wedding. As a thank you, Dorota asks Blair and Chuck to be the Happy Couple that escorts them into the chapel for good luck and Blair can't say no. Meanwhile, she hasn't told anyone except Nate what Chuck did to her, so she plays along like everything is okay but continually tells Chuck that she can't forgive him. At the wedding, Blair tells Chuck that she'll stay with him only because they're both sick twisted people who are fortunate to have found their match in each other. Before the wedding begins, Blair breaks down in front of Dorota and all the guests, admitting she and Chuck aren't happy and can't be the Happy Couple because they would only bring bad luck. After sitting down and talking with Dorota for a while, the wedding goes through perfectly and Chuck begs Blair to stay with him because they have to see their relationship through to the end. However, she breaks up with him anyway. Soon after, Jenny finds out that Serena's father, William van der Woodsen, is purposely prescribing Lily the wrong medicine to treat her cancer. Thinking it's a way to be close to Blair again, Chuck agrees to team up with Jenny to expose him. But when they go to Blair, she refuses to get involved with them and chooses to go out with her new friend, Cameron. However, she eventually agrees to help when she's approached by Dan and Nate, who are looking to acquit Rufus from accusations that he cheated on Lily. Together, they find that William was prescribing the fake medicine to keep her sick and coming for treatment so she would fall in love with him again. They successfully expose everything, and Chuck proposes a deal to Blair: that the next day, he'll be waiting for her on top of The Empire State Building and if she doesn't show by 7:01 PM, he is closing his heart to her forever. Blair informs him that she will not be there and goes home with Cameron (Ex-Husbands and Wives). In the season finale Last Tango, Then Paris, Blair tries to distract herself from The Empire State Building but after talking to Dan and continually catching sight of the building, she decides to go. But before she can, Dorota goes into labor and Blair escorts her to the hospital. By the time she leaves and gets to The Empire State Building, she finds Chuck gone and a bouquet of her favorite flowers, peonies, thrown in the trash can. Meanwhile, a heartbroken Chuck has returned to The Empire and has begun drinking. Jenny shows up, looking for Nate, and they sleep together to avoid feeling alone. Afterwards, Blair shows up in his penthouse and brings the flowers. Chuck sees that she did indeed go to meet him, and she explains that Dorota went into labor and had her baby. She also tells him that even though their relationship is complicated, love makes everything simple and they embrace, getting back together. Remembering that Jenny is still in his room, he offers to make Blair a drink. Inside his room, Jenny opens a bag on his nightstand and finds an engagement ring inside. She leaves, and Blair and Chuck head to the hospital to visit Dorota. In the lobby, Chuck is about to propose to Blair when Dan finds them and punches him for sleeping with Jenny. Blair quickly pieces what happened together and ends things with Chuck once again while also banishing Jenny from Manhattan. A few weeks later, it's shown that Chuck left for Europe and wound up in Prague, where he gets robbed by two thieves. He attempts to protect the engagement ring that he's still carrying, but they shoot him and steal it.
In the season premiere Belles de Jour, Blair and Serena are wrapping up their summer in Paris together. Blair mentions Chuck has been off the grid since they left New York and she just wants to have one nice date before they go home. Soon after, she meets Louis Grimaldi, a prince from Monaco. She goes on a double date with him, Serena, and his friend Jean Michele. However, the date ends after Blair learns Serena will also be attending Columbia University in the fall and Louis reveals he thinks Blair is only after his title. Afterwards, Blair confides in Serena that she's worried that she will never be able to move on from Chuck. Meanwhile, Chuck is on his way to Paris with a woman, Eva Coupeau, who saved his life after the shooting, and is pretending to be named Henry Prince.At the same time, Lily is concerned that she hasn't heard from Chuck, that he's ignoring his bills and business, and his credit card charges are not like him. After a body washes up in Paris with his ID, she has Serena go to the morgue to identify the body. She does so, and finds that the body is not Chuck's. The same day, Blair is out when she makes eye contact with Chuck, who is crossing the street. When both Blair and Serena return home, Serena tells about how she had to identify a body and that Chuck is missing, but Blair informs her that she saw Chuck herself. However, she is uninterested because she has convinced Louis to give her a second chance and they'll be attending a ball that night together. Serena is able to find Chuck, and begs him not to leave his life behind. He does so anyway, to pursue a future with Eva far away from New York. On the way to the ball, Blair stops at Harry Winston, where she runs into Serena and an investigator from Interpol. He explains that Chuck was shot while being robbed, and that things went so far because he was trying to protect an engagement ring that was purchased there. Realizing he was going to propose to her, Blair tracks down Chuck before he leaves Paris and announces that while she doesn't love him anymore, she can't have a life without him. The next day, she tells Louis that she can't try with him due to Chuck, but he can always come to Manhattan to find her. Meanwhile, Chuck reveals who he really is to Eva and asks her to come home with him (Double Identity). After everyone has returned to New York, Blair finds herself becoming increasingly jealous of Eva and her relationship with Chuck. At first, she attempts to make Eva unconfident in herself and her ability to fit in in New York, but fails (The Undergraduates). Soon after, in Touch of Eva, Blair learns that Chuck gifted Eva a very expensive Cartier watch. Knowing it might have cost more than anything he ever gave her, she heads to Cartier to see what she can find out. While there, she sees Eva selling the watch back to the store for cash. She takes a video and goes to see Chuck, where she shows him. He asks Eva about it, but she explains that the hotel's valet, Ivan, has a struggling family that is about to lose their family farm and she needed to help. Chuck forgives Eva, and asks her to choose a charity to donate five million dollars to. Blair goes along with her to try and get any incriminating information she can about her, and texts Serena to look into everything she learns. Along with Dan, Serena learns that Eva used to be a prostitute back in Prague. They tell Blair, who debates how to tell Chuck. Meanwhile, Dan lets it slip to Nate; who tells Chuck. He pretends he already knew, but later confronts Eva in private about it. At his gala later that night, Blair attempts to tell him but he tells her he doesn't care. At the same time, Lily has received Chuck's passport, cell phone, and wallet from the Paris police and given them to Ivan to give to Chuck. When Chuck announces that he's creating a new charity called The Eva Coupeau Foundation, Blair takes the items from Ivan to place in Eva's suitcase. She then tells Chuck that she found them in Eva's suitcase, and he goes down to investigate, where he indeed finds them; and thinks she knew who he was from the very beginning. Eva follows shortly after, and Chuck breaks up with her and tells her to leave New York. Devastated, he goes downstairs to have a drink, but learns from Lily that she just received his belongings and given them to Ivan. Realizing Blair set him up, he runs upstairs to catch Eva and apologize, but she leaves anyway. Afterwards, he goes to see Blair and declares all out war between the two of them. His first attempt at taking Blair down involves him wrecking her chances to assist visiting businesswoman Martha Chamberlain. However, it fails and Blair realizes he's serious about ruining her life (Goodbye, Columbia). Soon after, Jenny returns to New York to interview with Tim Gunn about possibly getting a recommendation to Parsons. Angry that she defied her orders to stay away, Blair orders her to leave; but eventually gives her a day pass, so long as she doesn't go anywhere but her interview and leaves right after. When Chuck learns Jenny is in town, he swipes her paperwork from the VDW's so she's forced to go to The Empire to retrieve them; knowing it will upset Blair. She does so, and in retaliation, Blair ruins her sample dresses and her chances with Tim Gunn. At a party that night, Jenny sends a tip to Gossip Girl about how she slept with Chuck, humiliating both Chuck and Blair. That night, they call a truce and end their war (Easy J). To ensure peace, Serena and Nate set them up to sign a peace treaty. They do so, and Blair invites Chuck to her birthday party that night. Meanwhile, Dan is sick of Blair and Chuck treating Jenny terribly and along with Eric, plots a way to bring them down together. Their first attempt, baiting Chuck with the possibility of Blair sleeping with Jack again, fails. However, he learns about their treaty from Nate and steals it before it can go into Chuck's safe. He goes through it with Eric and they find the perfect way to bring them down. At Blair's party, music artist Robyn and a professional roaster show up and broadcast a video of a drunken Blair singing backstage at a concert. Humiliated, Blair blames Chuck because he was the only one who knew about it. He denies doing anything, and Dan steps forward as the culprit. Later that night, they agree that their treat won't ever work and that they hate each other. After proclaiming their hate, they have sex (War at the Roses). For awhile after, Chuck and Blair continue to hook up but keep it a secret. They eventually realize they need to stop, with Blair wanting to quarantine herself from sex with Chuck and Chuck wanting to have an excess amount of sex to not want to anymore. However, neither plan works out and they continue to hookup (Juliet Doesn't Live Here Anymore). Meanwhile, they learn that their future endeavors could be put at risk if they were really together again, so they agree to keep it a secret. During one of their hookups, Chuck tells Blair he loves her; and she pretends not to hear. However, later that night she goes to his Saints & Sinners party and they share a passionate kiss in front of all party goers. Due to this exhibition, Blair loses any chance she had at taking over Anne Archibald's foundation, Girls, Inc. However, Chuck learns that things at the hotel are on the upswing and his publicist, KC, offers Blair multiple opportunities to be showcased as Chuck's girlfriend. Despite this, Blair tells Chuck that she needs to be successful in her own right before they can be together again and they promise to wait and see if they're truly meant to be together (The Witches of Bushwick). After Serena is hospitalized in Gaslit and they spend Thanksgiving together in the hospital, Blair admits to Chuck that she is now questioning their need to succeed on their own. Chuck tells her that he can't be her friend, even though he wishes he could. Despite this, she sends him a pie along with a note saying that even though they can't be friends, it doesn't mean they aren't. Soon after, old Bass enemy Russell Thorpe and his daughter Raina Thorpe arrive back in town. Chuck begins a tedious relationship with Raina that began as purely physical, but eventually it grew to be a romantic one. Once he learns that Russell is going to buy Bass Industries and dismantle it for parts, he works to make sure Raina falls in love with him. After he manipulates Raina into missing her business meeting about buying Bass Industries, he strikes out with her and Blair calls her to tell her that Chuck deserves a second chance because he is a good guy (Panic Roommate). On Valentine's Day in It-Girl Happened One Night, Chuck plans a lavish event to prove to Russell that Bass Ind. has equitable value and to woo Raina. At the same time, Blair, who is now working at W Magazine, needs to follow a socialite for a profile. She asks Raina, who originally agrees but backs out. However, Blair attends the event anyway and tells Serena that Chuck is only interested in Raina because he needs to save his company so seeing them together doesn't bother her. While there, she stumbles upon a private room decorated romantically that Chuck set up for Raina. She runs into Dan, and end up hearing a heated fight between Chuck and Raina; in which he tells her that she is sacred to him. Crushed, Blair realizes that he has real feelings for Raina. Afterwards, Blair begins to build a real friendship with Dan, which leads up to them sharing a kiss to find out if they have feelings for each other (Empire of the Son). After Raina begins dating Nate, Chuck realizes he really does want to be with Blair, but finds out she kissed Dan. When he confronts her, she admits that while it was life changing, it only was because it made her realize she wanted to be with him. She also tells him that even though she knows she's ready for them to be together and build a future, she knows he isn't ready yet; putting their relationship on hold once again (The Kids Stay in the Picture). Right after, Louis comes to Manhattan looking for Blair. They plan to attend a ball together to earn Louis' mother Sophie Grimaldi's approval so they can get engaged, but Chuck crashes it to win Blair back. He's escorted out, and Blair leaves due to being humiliated. However, Louis follows her home and proposes to her. She immediately accepts, and goes to The Empire to tell Chuck. When he finds out, he goes into a rage; which includes him punching a window in his penthouse, causing glass to go flying and one shard cuts Blair's cheek. Terrified, she runs out on him (The Princesses and the Frog). </p>Meanwhile, Sophie is suspicious of Blair and tells Louis that the first thing she did after getting engaged was go see Chuck. After finding this out, Louis decides to follow Blair and sees her with Chuck, warning him that Jack is back in town. At an engagement party thrown by Eleanor and Cyrus, Louis tells Blair to either meet him at Constance Billard's annual alumni gala prepared to share every part of herself, or not come and end it with him (Shattered Bass). Before she can go to Constance in the finale The Wrong Goodbye, Blair is lured to Chuck's new hotel site by Russell; to be burned alive in the building the same way his late wife was. However, Blair is able to reach Chuck via her speed dial and he arrives, along with Nate and Raina, to save her. When they're out of the building, they sneak into a bar mitzvah to have a drink and relax before she goes to see Louis. While at the party, they end up having sex and Blair tells Chuck that even though she's happy and secure with Louis, they don't have the passion that she has with him. After hearing this, he stops Blair from ending things with Louis and gives his blessing for them to be married. They admit that they will always love each other and say goodbye. A week later, Blair is about to leave to spend the summer in Monaco with Louis and Chuck is about to spend a Lost Summer with Nate. The last shot of the episode shows a positive pregnancy test in Blair and Serena's shared bathroom.</p>
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.Gone Maybe Gone, it's revealed that Chuck and Blair slept together that night in Monte Carlo, and 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, Chuck and Blair scheme 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 goes to see Chuck. At 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 thoughtIn 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. </p>
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'm sure the CIA would hire you in a second.
Chuck: Defending my country. Now there's a future I never imagined.
Blair: With good reason. What is she doing there?
Chuck: What is anyone doing there? It's a facility for the disturbed or addicted.
Blair: You must have your own wing.
Chuck: You don't get nearly enough credit for your wit.
-Poison Ivy (1x3)
Blair: You don't think I'd really go up there.
Chuck: I know you wouldn't.
Blair: Hold my drink.
-Victor Victrola (1x7)
Blair: Do you.. like me?
Chuck: Define like.
-Seventeen Candles (1x8)
Chuck: You looked pretty hot on Prince Theodore's arm today.
Blair: Is that what I am to you, just an accessory?
Chuck: Next to him, yes. On me, you'd be so much more.
-Hi, Society (1x10)
Blair: Isn't there someone else you can torture?
Chuck: Probably. But I choose you.
-School Lies (1x12)
Chuck: They say when you love something, you should set it free.
Blair: Ugh. They say when you hate something, you should slam a door in it's face.
Chuck: I love when you talk dirty, Blair.
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.
-Much 'I Do' About Nothing (1x18)
Chuck: Look, I never should 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.. 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.
-Summer Kind of Wonderful (2x1)
Chuck: Have sex with me.
Chuck: Just once, that's all I need.
Blair: You are disgusting and I hate you.
Chuck: So why are you still holding my hand?
-The Dark Night (2x3)
Blair: What took you so long?
Chuck: If you thought that was long, you have no idea what you're in for.
Chuck: Say it.
Blair: Say what, I'll say anything.
Chuck: Say those three words you wanted me to say.
Blair: Are you kidding?
Chuck: Not quite. Eight letters, three syllables, say it and I'm yours.
Blair: But I'm already yours and you're ruining the mood with all this talk.
Chuck: You can't say it. You wanted it from me.
Blair: Well, 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.
Blair: Is this because of Vanessa? It was a game, Chuck. That's it.
Chuck: Well, maybe I want to raise the stakes. Are you ready to play that game? I chased you for long enough. Now it's time you chased me.
-Chuck In Real Life (2x7)
Chuck: The reason we can't say those three words to each other isn't because they aren't true.
Blair: Then why?
Chuck: I think we both know that the moment we do, it won't be the start of something. It will be the end. Think about it. Chuck and Blair, going to the movies. Chuck and Blair, holding hands.
Blair: We don't have to do those things. We can do the things that we like.
Chuck: What we like is this.
Blair: The game.
Chuck: Without it, I'm not sure how long we'd last. It'd just be a matter of time before we messed it up. Look, I'd rather wait... and maybe in the future...
Blair: I'm sure there could be some excruciating pleasure in that.
Chuck: We're inevitable, Waldorf.
Chuck: I wouldn't change us. Not if it means losing what we have,
Blair: And what do we have Chuck? You tell me.
Chuck: Tonight. So shut up, and dance with me.
-It's a Wonderful Lie (2x12)
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're 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: Well that's too bad.
-O Brother, Where Bart Thou? (2x13)
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 want to do to yourself, please don't do that to me.
-In the Realm of the Basses (2x14)
Chuck: This isn't you.
Blair: How do you know?
Chuck: Because I know you better than I know myself.
-The Grandfather (2x19)
Blair: Last fall, you said we couldn't be together and I believed you. But every time 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.
-The Wrath of Con (2x23)
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 hear 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've hurt me too many times.
Chuck: You can believe me this time.
Blair: Oh.. that's it?
Chuck: I love you too.
-The Goodbye Gossip Girl (2x24)
Chuck: I'm not Chuck Bass without you.
-Reversals of Fortune (3x1)
Blair: I need that society. You don't turn down destiny.
Chuck: It's not destiny if you have to barter your way in. You're special enough on your own, you don't need some group to say you are.
Blair: And what about you? Since when does Chuck Bass pay for a partner? The Chuck I knew bribed no one but me.
Chuck: I've been meeting with the board of Bass Industries all morning. I told them I want to cash my shares out. Risk it all. They think I've lost my mind.
Blair: Have you?
Blair: Then how can you be so sure?
Chuck: Because you believe in me.
-The Lost Boy (3x3)
Chuck: Look, NYU is hard, but Blair Waldorf does not give up.
Blair: I'm not giving up. I've made a strategic retreat.
Chuck: Potato, potato.
Blair: You don't understand.
Chuck: I do understand. Let me help.
Blair: No, Chuck. NYU is not the Upper East Side. They don't care about Constance or the social hierarchy, they don't care that I'm Blair Waldorf! It's over.
Chuck: And you do this to me.
Blair: What are you talking about?
Chuck: I'm Chuck Bass. And I told you I love you. You're saying that 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.
-Dan de Fleurette (3x4)
Blair: Are you upset because you kissed a guy?
Chuck: I'm upset because I kissed somebody who wasn't you. Do you really think I've never kissed a guy before?
Blair: Love me?
-Enough About Eve (3x6)
Chuck: Blair. You and I both know you'll never be completely trustworthy. I admit it's not my strong suit either, but it keeps things interesting between us.
-How to Succeed in Bassness (3x7)
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. Ran 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. But you aren't 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. Come. Let's say goodbye.
-The Debarted (3x12)
Chuck: I spent 18 years accepting the fact my mother was dead. It was misguided to let one of my father's girlfriends allow me to question that. TO hope things may be different.
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.
Blair: That doesn't mean you're alone. I love you, Chuck, and I'll always be your family.
-The Hurt Locket (3x13)
Blair: Please tell me Jack was lying. You wouldn't betray me like that.
Chuck: Me betray you? You're the one who just came from seeing my uncle!
Blair: I went there for you. Because I thought it was the only way to save your hotel. I would've done anything to help you. All you had to do was ask.
Chuck: If I had asked, it wouldn't have worked. You would have been too willing when Jack came to you, and he would have known we were working together. I did what I had to to win.
Chuck: I can't let my feelings cost me all that I've built.
Blair: Even if it means losing me instead. All I ever did was love you.
Chuck: The worst thing I ever did. The darkest thought I ever had. You said you would stand by me through anything. This, Blair, is anything.
Blair: I never thought the worst thing you would ever do would be to me.
Chuck: You went up there on your own.
Blair *slaps him*: Goodbye, Chuck.
-Inglourious Bassterds (3x17)
Chuck: Blair, you and I are magnetic. You can feel it. Our pull is as undeniable as ever.
Blair: It's different this time.
Chuck: It doesn't have to be. I love you. Saying it was hard, but I did and I've never looked back. So now I'm asking you: please do this for me. Please forgive me.
Blair: I'm sorry, I can't.
Blair: Everything you said last night was true. We do belong together. We're both sick and twisted. If you think about it, we're incredibly fortunate to have even found each other.
Chuck: Blair, I don't want this to be you settling, some sort of consolation-
Blair: We've both his rock bottom, Chuck. But we've hit it together. At least we won't be lonely in hell.
Blair: I want what Dorota and Vanya have. Real love. Pure and simple love.
Chuck: You'd be bored within five minutes.
Blair: Better bored than ashamed of myself. I would do anything for you, Chuck, but what if that's wrong? I never thought it was possible to love someone too much but maybe it is. I don't like who I've become with you.
Chuck: Wait, Blair.. don't bail on me. We have to see this through to the end.
Blair: This is the end, Chuck.
Blair: I wasn't going to show up. I was resolve not to. Every bone in my body tried to slow me, every voice in my head screamed don't.
Blair: But I didn't listen. I followed my heart because I love you. I can't deny that our path has been complicated but in the end love makes everything simple.
-Last Tango, Then Paris (3x22)
Blair: Just because you're dressed poorly doesn't mean you're not Chuck Bass.
Chuck: Why would I want to be him?
Blair: You should've told me you got 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 want to know.
Chuck: When I woke up my ID was gone. Nobody knew who I was, nobody was coming to look for me. I realized 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 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.
-Double Identity (4x2)
Chuck: I know what you did, Blair. It's despicable. Even for you. Do you hate me so much you can't stand to see me happy?
Chuck: So why did you drive the one person I care most about out of town?
Blair: Eva left? Chuck, I never meant to-
Chuck: Make her leave me? Of course you did. I need to know why. Is it possible you still love me?
Blair: How could I still love you after what you did?
Chuck: So you did it just to hurt me. Eva made me into someone I was proud to be, you just brought back my worst self. This means war, Blair. Me vs. you. No limits.
-Touch of Eva (4x4)
Blair: If you're here to deliver any further humiliation, Dorota can sign for it.
Chuck: Jenny was right. If we keep going, we'll both end up dead and I like myself too much to let that happen. I assume you feel the same way.
Blair: About myself? More. What do you suggest?
Chuck: A truce.
Blair: Why don't you just skywrite the word "double crossed", it would be more subtle.
Chuck: Look, we can keep blaming each other for what happened that night, or we can admit a harder truth. It was no one's fault. It was fate. Tragedy.
Blair: If Serena hadn't kissed Dan, Nate wouldn't have been at the hospital looking for her, and Jenny wouldn't have gone looking for Nate.
Chuck: If Dorota hadn't gone into labor..
Blair: Maybe everything would be different. But it's not.
Chuck: We're holding on to the pain because it's all we have left. But we don't have to. We have a choice.
-Easy J (4x6)
Chuck: I wanted to let you know the treaty is over.
Blair: Fine with me. This pretense of civility was exhausting.
Chuck: Being amicable isn't in our blood. I've realized we aren't friends. Friends have to like each other. And after what happened tonight, I could never like you.
Blair: I could never like you either. In fact, I hate you.
Chuck: I've never hated anyone more.
Blair: Every nerve ending in my body is electrified by hatred.
Chuck: There is a fiery pit of hate burning inside me ready to explode.
Blair: So it's settled then.
Chuck: We're settled.-War at the Roses (4x7)<p>_______________________________Chuck: I love public.
Blair: I love condemnation.
Chuck: I love you.
Blair: ....Of course, no one does black like Dior.
Blair: As long as I'm with you, I'm Hillary in the White House, and I want to be Hillary, Secretary of State, but with better hair.
Chuck: Then you'll find another way to show the world you're a force to be reckoned with. We'll build our futures together.
Blair: I followed my heart all last year and it led me nowhere. Now I have 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: If two people 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.
-The Witches of Bushwick (4x9)
_______________________________Blair: This looks like the dress Diana wore the day after she became princess.
Chuck: Yes. I wanted you to wear it in the photo with me. I had no idea I could just ask. It's not too late. You don't have to be powerful on your own first, we can build our futures together.
Blair: The saddest part is that I'd come to the same conclusion. But now that I know I'm ready, I realize you're not. I thought that everything you went through: Prague, Eva, Russell, that maybe you'd changed. But.. who was I kidding.
Chuck: Don't say that.
Blair: You have years before you're capable of a real relationship, if you ever will be. I'm sorry, Chuck.-The Kids Stay in the Picture (4x18)
_______________________________Chuck: There's a difference between a great love and the right love. I left The Empire State Building last year two minutes after you didn't show. Louis waited all night. This is your chance at happiness. You think you shouldn't want it because 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 ever let anyone tell you you're not powerful. You're the most powerful woman I know.
Blair: It's taking all the power I have to walk way 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.
-The Wrong Goodbye (4x22)
Blair: If I know anything about Chuck Bass, it's that fatherhood is not part of the lifestyle.
Chuck: You must have been very relieved when you found out 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 sent him to get fixed, I thought it was the responsible thing to do.Blair: I should go... Louis' waiting for me. There's a part of me that really wanted it to be yours.
-The Jewel of Denial (5x3)
_______________________________Chuck: 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. But 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 gonna be my downfall.
Chuck: It'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 gonna change.Chuck: It's okay if it has to. Starting tonight, I'm going to take care of myself.
-I Am Number Nine (5x6
_______________________________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.
-Rhodes to Perdition (5x9)
Blair: I have to tell Louis face to face that the wedding is off.. he deserves at least that.
Chuck: Are you sure you want to do this? A prince, a fairy tale wedding, this is all you ever wanted.
Blair: No.. you're all I ever wanted. I love you. I love every part of you. I-I couldn't tell Louis that he wouldn't ever lose me because it wasn't true. You're the one I never want to leave.
-Riding in Town Cars With Boys (5x10)
Blair: I just came to tell you what a wonderful person you've become. And I hope you won't let this change that.
Chuck: Well don't leave me.
Blair: I'm not doing it to hurt you.
Chuck: You sat in the car and you said you'd never go. We were going to spend the rest of our lives together and now you can't even look at me. Now you.. don't even care enough to tell me why?
Blair: I saw what was important and I made the only choice I could.
Chuck: If it's not an affair with Humphrey, something else changed you, what was it? Cause love does not just disappear.
Blair: We can never be together. Please, Chuck, just move on and be happy.
Chuck: I can't. Until I know why, I won't stop. I will use all the power I have to find out the truth.
Blair: Some things are more powerful than even you. I'm sorry. Don't let this destroy all the good in you. Just because we can't be together doesn't mean I won't love you.
-The End of the Affair? (5x11)
Chuck: Don't marry him.
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 aren't 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 not that simple.
Chuck: It's only that simple, you told me you love 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 everyday if it's even possible to love someone that much.
Chuck: Then 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: Hey, don't worry. I'll protect you from Louis and whatever his mother threatens, if there's a dowry I'll pay it.
Blair: I can't let you buy my freedom.
Chuck: If it means getting rid of them, it's worth whatever the cost. I'd do anything for you.
Blair: No.. not like this. I made a promise and I need to keep it.
Chuck: To God? Please. You broke that promise when you left Louis. And look, I'm still standing.
Blair: Chuck, I need you to let me handle this on my own. What kind of chance do we have if our fresh start is you buying me from Louis? When and if we end up together, it has to be as equals, with nothing over our heads. That's the only shot we have.
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.
Blair: Louis won't lay a hand on me. I promise. I'm sorry. This is how it has to be.
-The Backup Dan (5x14)
Blair: And I love you. I always will. But that doesn't mean I'm in love with you. At least not right now, not the way you need me to be, not the way you deserve. I'm sorry.
-The Princess Dowry (5x17)
Blair: You fought for me all year. I've come to fight for you.
Dealer: Will you be joining the game?
Blair: You said I always bet against you but this time I'm all in.
-The Return of the Ring (5x24)
Chuck: Blair, I love you with all my heart and that is the reason we cannot take the chance of messing this up.
Blair: Sure, cause what would your father think if you failed? That I distracted you. That you sacrificed your empire for me.
Chuck: Blair, you are a distraction. Cause 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. After a couple nights in Monte Carlo, I lost track of all time.
Blair: We were exhausted and starving. I think I had an actual fever.
Chuck: But that's not why we need to do this, and neither to prove a point to my father.
Blair: Then what?
Chuck: In the past, I blamed my mistakes on you and Bart was right on that count. It's the boy who blames the girl, not the man, and that's what I want to be with you. It won't be much longer. I promise.
-Gone Maybe Gone (6x1)
Blair: I'm all yours. Mind, body, and scheme.
-Dirty Rotten Scandals (6x3)
Chuck: Will you go to war with me?
-It's Really Complicated (6x8)
Chuck: Just have faith in me. This one last time.
Blair: But I've waited too long and I need to be with you now!
Chuck: Blair, trust me. Letting me go is the right thing to do.
Blair: No. 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.
-The Revengers (6x9)
Blair: Jack is right. Chuck and Blair hold hands. Chuck and Blair go to the movies. You said you never wanted us to be boring.. well, we definitely aren't that now.
Chuck: I was a stupid child when I said those things.. A life with you could never be boring. Blair Cornelia Waldorf.. will you marry me?
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!
-New York, I Love You XOXO (6x10)
- They won the Hollywood Life poll for Hottest TV Couple.
- They won the Hollywood Life 25 Hottest TV Couples Poll in 2012.
- They won the Hollywood Life for The TV Couples We Want to See Together Poll in 2012.
- They won the Wetpaint Poll of the Sexiest Couple on a Scripted TV Show.
- They won EW's Sexiest Couple on Network TV Poll.
- They won BuzzSugar's Poll for The Best TV Romance of 2009.
- They won BuzzSugar's Poll for The Best TV Romance of 2010.
- They came in 5th in Portrait Magazine's Top 10 Couples of 2007-2008.
- They won Portrait Magazine's Top 10 Couples of 2008-2009.
- They won Portrait Magazine's Top 10 Couples of 2009-2010.
- They came in 4th in Portrait Magazine's Top 10 Couples of 2010-2011.
- They won Portrait Magazine's Top 10 Couples of 2011-2012.
- They won Portrait Magazine's Top 10 Couples of 2012-2013.