|Full name||Charles Bartholomew Bass|
|Nickname(s)|| Charles (by Lily) |
Chuck (by everyone else)
Henry Prince (Alias)
C, Bass Jr.
|Birthplace||Manhattan, New York City, NY|
|Birthday||January 19, 1991|
|Occupation|| High school student |
(at St. Jude's; graduated)
|Family|| Blair Waldorf|
(wife; 1 child)
(son, with Blair Waldorf)
Bartholomew "Bart" Bass
Lillian "Lily" van der Woodsen
Serena van der Woodsen
Eric van der Woodsen
|Romances|| Blair Waldorf (wife) |
Vanessa Abrams (one-night-stand)
Eva Coupeau (ex-girlfriend)
Raina Thorpe (ex-girlfriend)
Jenny Humphrey (one-night stand)
Georgina Sparks (one-night stand, lost virginity to)
Alessandra Steele (fling)
Josh Ellis (kissed)
|Friends|| Blair Waldorf|
Nate Archibald (best friend)
Serena van der Woodsen
|Enemies|| Louis Grimaldi |
|Portrayed by||Ed Westwick|
|Last appearance||"New York, I Love You XOXO"|
Charles Bartholomew "Chuck" Bass is a main character throughout the Gossip Girl television series and is also recurring character in the novel series of the same name. Chuck Bass is portrayed by Ed Westwick in the television show.
Chuck appeared in 117 episodes.
He is on the front with his love for Blair Waldorf.
He is married to Blair Waldorf the love of his life and is best friends with Nate Archibald. He is also good friends with Serena Van Der Woodsen and Dan Humphrey.
Chuck Bass was born on 19th January 1991 and grew up as the only child of Bartholomew "Bart" Bass, a self-made billionaire who owns the New York Palace Hotel. Chuck lived amongst equally privileged childhood friends Nate Archibald, Blair Waldorf, and Serena van der Woodsen. Chuck is generally shown throughout season 1 and season 2 as the group's bad boy, and is frequently manipulative. However, later in his Junior and Senior year, a softer side to his personality formed more for people cares about, most notably Nate and Nate's long-time girlfriend Blair. He often blames himself for his mother's death even though it isn't his fault, he has a tendency to not completely trust people and always has to aim better than he can achieve.
Chuck Bass is orphaned in his senior year at high school due to the death of his father in a car accident, causing him to go off the rails like he had been before, being adopted by Lily Bass Humphrey, his step-mother and the closest mother figure he'd ever had.
In the Gossip Girl novels, Chuck has a series of flings with female characters across the course of the series. Chuck's role is initially that of an antagonist to the main characters. Chuck resides with his family at the Plaza Hotel on the Upper East Side and attends school at the Riverside Preparatory School for Boys on the Upper West Side, along with scholarship student Dan Humphrey. Chuck is largely friendless but is tolerated by the others because of his family's enormous wealth. He is described as having flamboyant fashion sense, with a penchant for scarves. Lazy and vain, Chuck's only interests are sex and money, and he is frequently chided by his father for lacking ambition and performing poorly in school. Following flings with numerous females and males, his only serious relationship comes near the end of the series, when he begins dating Blair Waldorf, a self-obsessed luxury loving teenager. In the twelfth book in the series, Gossip Girl: It Had To Be You (2007), Chuck is rejected from colleges because of poor grades and is sent to military school by his father. When next mentioned in Gossip Girl spin-off The Carlyles (2008), it is stated that Chuck never showed up to military school, and his whereabouts thereafter are unknown. In the thirteenth Gossip Girl novel, I Will Always Love You (2009), it is revealed that Chuck went off to Deep Springs College in California and returned a changed man and to have dated main character Blair Waldorf in Oxford, England for a year. Chuck also owns a dog named Monkey which is generally always with Chuck. In the novel, Charles is the son of Bart and Elizabeth Bass.
As the show opens Chuck is portrayed to enjoy seducing women and who uses them to keep himself entertained when his best friend Nate or his heartless father are not around.
Chuck Bass was then reconfigured as a more central character, an antiheroic heterosexual playboy whose on-off relationship with Blair Waldorf serves as one of the show's major ongoing storylines. Chuck is the resident "bad boy" of the Upper East Side, and like Blair is both vengeful and manipulative; the two often scheme elaborate plans together. As the show progresses, Chuck develops a softer side, specifically towards Lily his step-mother, Eric and Serena, Chucks step- brother and sister, Nate, his lifelong best friend, and Blair, the love of his life.
In the first episode Chuck hits on Serena, who has just returned from a year at boarding school. She rejects his advances and storms out on him, and he isn't seen to have any physical attraction to her after that. In the same episode Chuck also tries to force himself on Jenny Humphrey at the Kiss on the Lips party that Blair is hosting. However, he is stopped by Serena and Jenny's older brother Dan, to whom Chuck takes an immediate dislike. Chuck was the only one who knew about Nate and Serena's one night stand, one of the reasons for her leaving town for the year. However, a furious and hurt Blair also found out and told Dan in the episode The Wild Brunch.Chuck has a strong loyalty to his lifelong best friend Nate, bailing him out when Nate loses a risky poker game with Carter Baizen. Chuck says that the only things that matter to him are money, the pleasures money brings him, and Nate. However, Chuck was close childhood friends with Serena and Blair, too. Together, Chuck, Blair, Serena and Nate all joined forces and enlisted themselves as the Non-Judgmental Breakfast Club. However, Chuck attempts to rape Serena in the pilot episode. Shortly afterwards, she breaks up with Nate because of his recurring feelings for Serena. Blair goes out to Victrola, the burlesque club that Chuck has recently purchased for his fathers company. They share several drinks together, and he then challenges her to dance onstage, a dare that she accepts. Blair, who is relieved by her breakup with Nate, is finally able to let loose and dances seductively, while an impressed Chuck watches the real Blair finally show. At the end of the night, Chuck gives Blair a lift home in his limo. He compliments her dance by saying "you were amazing up there," Chuck's words make Blair feel wanted and beautiful and they both forget about the outside world for a moment when Blair approaches Chuck for a kiss. Chuck pulls away shortly and asks Blair if she is sure, knowing she may just be feeling vulnerable from her breakup with Nate. Then Blair starts passionately kissing him. Blair loses her virginity to Chuck in the back of his limousine. The next day Blair goes to confessional at chuch and admits that she is guilty about both her performance at Victrola and night with Chuck in the limo. She leaves the church only to find Chuck, who has been looking for her and he tells her that he enjoyed the previous night. Blair on the contrary tells him for her that night never happened and warns him to not tell anybody, and once more reconciles with Nate. On Blair's seventeenth birthday, Chuck pulls her aside and admits his unfamiliar feelings for her, mentioning that he feels sick and can't sleep because of thoughts of her and their night togetherThis leads Blair to freak out in disbelief. A couple of hours later, Nate fails to show up to the party, instead talking with Jenny. Photos of them hugging are sent around by Gossip Girl, although Jenny is not identifiable, leading Blair to hide out in one of the bedrooms. Chuck comforts her gives her a present, the diamond necklace that Blair had put on hold that day of her birhtday and been expecting from Nate. Chuck compliments her while putting that necklace around her neck that saying to her"something this beautiful deserves to be seen on someone worthy of its beauty." Their undeniable attraction takes hold of them and they begin to kiss passionately on the bed. This begins their secret love affair.
At the debutante ball Chuck starts to worry that he will lose Blair to Nate again. Discovering that Nate is pursuing Blair again and asking Chuck all these questions about Blair one being "Is she seeing anyone", Chuck attempts to manipulate the events in his favour. Knowing that Blair considers Nate a gentleman who would never cause a scene, he manipulates Nate into punching someone at the ball saying to him "he's telling her what he is going to do to her tonight". When Blair finds out that Chuck was behind it, she finds and sleeps with Nate. Heartbroken, Chuck leaves New York for a while.
When Chuck returns he is shown as jealous, threatening to tell Nate about his relationship with Blair. Blair challenges him, saying she would like to see him try. Vanessa Abrams, in Chuck's favor, catches this conversation on tape while filming a documentary for a project. Trying to make it up to Blair, Chuck buys the tape from Vanessa for ten thousand dollars. However, this tape is actually blank, and Vanessa gives Blair the real one for free. Chuck still doesnt give up and chases Blair only to hear from her that whatever happened between them she could hardly recall. A disgusted Chuck then decides to exact revenge by sending a tip to Gossip Girl, saying that Blair slept with two guys in only one week. The news spreads like wildfire, and ruins Blair socially within hours. After seeing the bulletin, Nate finds Jenny and asks if it's true. Jenny, tired of being treated terribly by Blair, tells him that Chuck and Blair slept together. This leads to Chuck and Nate getting into a fight outside the school, with Nate ending his friendship with Chuck and his relationship with Blair. Blair turns to Chuck when there's no one else, but he rejects her, saying she used to be fascinating to him when she was pure and untouched, but not anymore.
Chuck's father and Serena's mother become engaged, leading the two families to move in together. He is annoying to Serena, particularly because he smokes marijuana in her bathroom. He also becomes a brother figure to Eric, something that Serena isn't very happy about. At a family dinner, Serena receives an anonymous package, which she opens at the table. It's filled with pornography, and she gets mad at Chuck, thinking he is the one who sent it. Chuck insists that he isn't responsible for the package, but is given a warning by his father. When at school, three crates of champagne are delivered anonymously to Serena, who again blames Chuck for it. The final straw comes when Eric gives her another one of the unsigned packages, this one is a baggie of cocaine. She tells her mother, and Bart kicks Chuck out of the apartment. Just afterwards, Serena realizes that it wasn't Chuck who was sending the packages after all, but her ex-best friend Georgina Sparks.
Serena spirals out of control after Georgina continues to blackmail her, and when she spends all night partying, Blair enlists the help of Chuck and Nate, despite the fact that they hate each other because of Chuck and Blair's affair. It is revealed that Chuck lost his virginity to Georgina in the sixth grade and he's been "running from the crazy bitch ever since." Even though things are still tense between them, Blair suggests that she and Chuck personally find and exact revenge on Georgina. Chuck agrees to this, responding, "Let's get the bitch." When they arrive at the Lincoln Hawk concert, Georgina has already left with Dan, who has since broken up with Serena after she lied to him. At his father's wedding to Serena's mother, Chuck alerts Nate when he sees the Captain, Nate's father, appearing to buy cocaine. This causes the two friends to make up and for Chuck to confess his love for Blair. Nate realizes that Chuck's feelings for Blair are genuine and gives his blessing. While giving his best man speech, Chuck is inspired the moment he looks at Blair and puts down his note cards, instead talking about true love and perseverance and forgiveness, inspired by his complex relationship with her.At the wedding, Blair forgives him for blogging about their relationship to Gossip Girl and subsequently abandoning her and he tells to her that she doesn't belong with Nate and that she never has and never will. The two then kiss passionately and begin a relationship, Chuck decides to "take it slow and do it right this time", which shows Blair that he is a romantic at heart. Chuck's father, Bart Bass, sees the new relationship as an opportunity for Chuck to mature and abandon his decadent lifestyle. Listening to his father and afraid of the commitment he will have to make to Blair, Chuck has second thoughts about his and Blair's summer plans to go to Tuscany, thinking Blair would not like the real him. He decides not to go and seduces the Bass' interior designer. Blair, unaware of Chuck's intentions, boards the jet to Tuscany, believing that Chuck will catch the next commercial flight.
In the season two premiere Summer Kind of Wonderful, we learn Blair has stayed in Europe over the summer. Because of his fear of committing to Blair, Chuck has stayed in the Hamptons trying to get over Blair by sleeping with a different girl every day. When she returns, he realizes that he regrets his actions; however, it is too late, Blair has begun a relationship with Marcus Beaton, a British Lordwhom she met on the plane. At the Vitamin Water White Party, while Blair is waiting for Marcus to pick her up, Chuck reveals that he was afraid that if they spent the entire summer together, she might see who he really is. Blair then says that she will belong to him and him only, if he tells her he loves her. He ultimately can't expose himself in that way and Blair leaves with Marcus.
In "The Dark Night" Chuck is having problems with his sexual performance and notices he won't be "cured" until he sleeps with Blair. During a blackout at a party, Chuck asks for Blair to sleep with him only one time but Blair refuses, even though Chuck notices she doesnt stop holding his hand. Blair and Chuck begin to kiss passionately during the blackout and apparently she thought it was Marcus, but as he walked in on them she says that she knew it was Chuck all along. Later Chuck is kissing some woman back in his limo but says to her that it's not gonna work. When she asks "I thought you said you're better" Chuck answers "I am..just not for you." refer to the fact that he's still isn't over Blair.In New Haven Can Wait, while everyone else is visiting their prospective colleges, Chuck and Nate stop at Yale University. He hopes to run into the "Skull and Bones" group, who eventually kidnap him. He wants to become a member, and in order to do so, he must show his "worth" in several ways, including giving up Nate (who is hated by several because his embezzling father lost their families' money). Instead of betraying his best friend, Chuck sends them to Dan, telling them he's Nate. The Skull and Bones kidnap Dan, take off his clothes (except for boxers) and tie him to a statue. When Nate hears what he's done, Nate ends his friendship with Chuck and befriends Dan, leaving Chuck alone.
In episode O Brother, Where Bart Thou? Chuck, maddened with grief over his father's death and angry at Lily, his stepmother, for cheating on his father, attends his fathers funeral extremely inebriated. While there, he says that he has no family and refuses to talk to anyone rationally. Enraged, he leaves the wake to flee to a bar, but Blair follows him. She wants to go with him to support him, saying that she will stay with him no matter what and finally declares her love for him. After being hurt so much, Chuck is unable to admit his feelings and leaves Blair alone on the street. He goes to her house the next day, seeking comfort and solice. He cries in her arms and they fall asleep on Blair's bed. However, when Blair awakens, Chuck is gone and left only a note that said how sorry he was and that she deserves better. Chuck has fled to Thailand.
Month later, Chuck's Uncle Jack brings Chuck back from Bangkok and Blair continually tries to help him get over his father's death, eventually talking him down from the edge of a building, saying that she'd always be there for him. When his father's will is read, it is revealed that his father has left him Bass Industries. However, his Uncle Jack sets Chuck up so the board will see his partying ways, and so Jack wins the company. When Chuck goes to see Blair, she tells him she 'can't watch him self-destruct any longer'. Chuck leaves her house dejected.
Chuck teams up with his stepmother Lily to get rid of Jack, and they come up with the perfect way - Lily becomes his legal guardian, as Bart and Lily were already planning on adopting each others' kids anyway before Bart died. Chuck signs the papers, and Jack, who is high on what is later revealed to be a "combination of meth, alcohol and over the counter cold medicine", becomes enraged and tries to rape Lily in the ladies' room at the opera. However, Chuck gets there in time and punches his uncle in the face to subdue him. He decides to move back into his old home with his family: Lily, Serena and Eric.
Chuck is jealous and hurt when Blair begins date Nate again, and goes to Nate's ex girlfriend Vanessa for help. However their plan to break Blair and Nate up fails and the two end up sleeping together. Chuck then runs into Blair on the street and they begin plotting against Serena's new boyfriend Gabriel (who turns out to be a con artist). Jealously, Nate asks Blair to move in with him, but Blair doesn't answer, which leads Nate to confront Chuck about his constant proximity to Blair - he says that if he wants her, he should man up and tell her, and if he doesn't, he has to cut her loose, because Nate wants her himself. Right after that, Chuck decides to talk to Blair. She tells him she can't answer Nate's question, until Chuck tells her how he truly feels about her. Blair says that if he doesn't love her, he has to let her go, and begins to cry. He tells her it was just a game, and Blair walks away thanking him. Serena witnesses this conversation and when she questions him about it, Chuck tells her that he loves Blair but thinks he can't make her happy, so he let her go. However, Chuck gives Blair her dream prom, and proves to himself that he in fact can make her happier than Nate can.In the season two finale, it is revealed to everyone that Chuck slept with Vanessa and Blair slept with Chuck'suncle Jack so that he could find Chuck and bring him back. Blair tries to explain to Chuck why she did it and that she loves him and if he says it back all of the gossip and lies and the hurt would have been for something, Chuck only says that maybe it was but it's not anymore. Chuck runs away to Europe, hurt.
However, one week later he returns to New York and goes to see Blair with presents for her, and he finally tells her that he loves her. The two share a passionate kiss while Chuck keeps telling Blair that he loves her, and it is implied they were then in a relationship.
Serena wants to get back at Chuck for telling Rufus about Brown, and with the help of Carter, sabotages another meeting by discouraging Chuck's business associates with sordid stories from his past. Leaving, Chuck says he only told Rufus about Brown because he was worried about her.
Chuck begins to be immersed in his work. He's even too busy to spend quality time with Blair, blowing her off for getting ready for a meeting with Sean McPherson, the owner of a hotel club Chuck wants to buy. At this meeting Chuck is given the cold shoulder from McPherson's assistant Daphne, who tells him that in order to even get his foot in the door, he must demonstrate respect for McPherson's past. He sees a Soethby's catalog with a photo flagged and decides the best way to get in McPherson's good books is to bid on and win the photo for him. Only it turns out that Blair needs the same exact photo in order to be accepted into a college society. As a result, Chuck and Blair have a bidding war for the photo at the auction until Serena ends up outbidding them in an attempt to stop their fighting. It is revealed that the pair had been sabotaging Carter to protect her. Serena ends up giving it the photo to Blair, who then gives it to Chuck. She tells him that she believes in him. At McPherson's office Chuck deduces that Georgina set him up to go after that photo and Daphne, the assistant, who is also friends with Georgina, confirms it. He hands the photo to the head honcho and then leaves.
Chuck tells Blair that, as she believes in him, he's ready to think a lot bigger - he's cashing out his shares of Bass Industries and is going to buy the whole entire Empire Hotel, not just the part he wanted to put a club in. He then invites her to go and 'christen' the penthouse.
Chuck notices that Blair is dealing with her insecurity at not having friends at NYU by immersing herself in the Queen Bee drama at Constance Billard, her alma mater. When Blair denies it, he goes to Jenny for help. They plot about how to bring Blair back down to Earth and how to restore order at Constance, where he wants Jenny to reclaim the role of queen. Chuck ends up bringing Jenny as his date to the movie premiere of "Fleur", causing Blair to be temporarily humiliated. When Blair shows up at the premiere to let Jenny have it, Chuck confesses that it was all his idea. He says he did it because he thinks she is selling herself short and needs to remember she's Blair Waldorf. If she can make Chuck Bass admit he loves her, she can win over NYU in due time. He also paid a photographer to take pictures of Blair at the premiere so that she would get her confidence back. Chuck also sends a school girl outfit to Blair's penthouse, with a note telling her that he needs some "tutoring".
In episode Enough About Eve, Blair's plan (which is to get to toast at the Freshmen Dinner at Parent's Weekend) involves re-instituting her and Chuck's game from the summer… with a little twist. Blair tells Chuck that she needs him to seduce Josh Ellis so she can humiliate him, as he double-crossed her, and Chuck goes along with it. Blair interrupts the scene right after the big kiss and pretends to make a big scene. In reality, she had made a deal with him; she gets to make the toast, and he gets to kiss Chuck Bass. Chuck's plans get canceled, so he shows up at the dinner and gets a little too much info from one of Blair's new minions. Then he sees Blair and the man he kissed talking and laughing and he realizes something is definitely up. Blair's plan is revealed when Vanessa hides a microphone in her purse, and her nasty rant about Vanessa is aired to the entire audience, including how she used Chuck to get the speech. Blair goes over to Chuck's to apologize and it is clear he needs some more time to think about it.
In the next episode, Chuck and Blair are talking again, though he is still chilly towards her. Chuck is trying to find a way to boost his hotel's ratings and decided to open the club. He calls Serena for help, as she works for a publicist and has PR experience, but instructs her to leave Blair out of it (not knowing that Blair is listening to the conversation). Blair calls Jack Bass and gets him to send over a liquor license for Chuck, desperate to help out. Later, Chuck comes to Blair's and gives her a costume for the club's opening (a flapper dress for the event's 20s era, Prohibition-theme), and they briefly make up. This is ruined when Chuck finds out she called Jack. Chuck tells her that he kept her out of opening the club for the same reason it took him so long to tell her he loves her; he can't trust her. He uninvites her to the opening but Blair shows up anyway after finding out the liquor license Jack sent over was a fake. Blair apologizes to Chuck and tells him that she was trying to make him see that he needed her. Chuck tells Blair that he already knew the license was a fake, and the two quickly come up with an idea. Chuck calls the police and has them shut down the club, while Blair makes sure the paparazzi gets pictures of the celebrities present. Chuck decides to open a secret club, and by the end of the episode Chuck and Blair have made up.
In the episode The Debarted, it is the anniversary of Bart Bass' death and Chuck wrestles with the dilemma of following his conscience or that of his father. All day he is very agitated with everyone, especially Blair who wants to comfort him and thinks he should visit his father's grave. He even has visions of his father, who berates Chuck for being soft and not having the keen business sense that he has. He finally throws Blair out of his suite so that he can brood alone and ignores her calls for the rest of the day. When on the way to a big business meeting, he finally answers one of her calls and learns that Serena has been in a car accident. He turns his limo around and goes to the hospital much to his father's ghost's dismay, and he finally blows up and screams at his father to "leave him alone." The ghost vanishes. When he enters the hospital, he is overcome with emotion and is reminded of when he came to see his father right before his death. Blair finds him sitting in the hospital floor. Being concerned of his family, he asked Blair about Serena's condition and if Lily and Eric were there. She tells him that everyone is there and comforts him, telling him that he has become a man in ways that his father never was and pulls him back up. Later, while visiting his father's grave he see's a Mystery Woman lying yellow roses, his father's favorite flower, on his gave.
In the episode The Lady Vanished, Chuck learns that Mystery's Woman's name is Elizabeth Fisher and she may be his mother. He spends a lot of time and resources, including using his private investigator to find out who she is, and bribes several hotel employees to get more information about her. She eventually reveals that she is his mother, and after a brief falling out when Chuck believes she just wants his money, they become very close.
In the episode The Empire Strikes Jack Chuck finds himself once again at odds with his uncle, Jack Bass, who is behind several untrue sexual harassment lawsuits against Chuck. Chuck worries that his mother will think less of him as a result of the slander, but she is supportive. When he invites her to a benefit for his late father, she declines due to fears of running into his uncle Jack. When he brings up Elizabeth when talking to Jack later, Jack tells Chuck that he was there when his mother was buried, and that she's playing him, causing Chuck to test the DNA on a glass she had drank from to find out for sure. When Chuck's lawyer tells Chuck that a Christian organization is planning a boycott against the Empire as a result of the sexual harassment lawsuits, he advises that Chuck sign over the company to a family member until things quiet down. Jack interrupts and nominates himself, but Chuck refuses him, as well as Lily, because he doesn't want it to seem that Bass Industries is bailing him out. When the DNA results come back positive, Chuck decides to sign over the hotel to his mother, not realizing that the lawyer and his mother had been working with Jack Bass to gain the hotel, using the harassment suit as part of the scheme. Elizabeth, who is in love with Jack, signs the hotel over to him, although she seems to have a change of heart later on. Jack has Chuck removed from the Empire's penthouse, and Chuck and Blair scheme to come up with a way to get the Empire back. Elizabeth, disgusted with what she has done, tells Chuck that she lied to him, and isn't his mother, and leaves New York for good, although a conversation with Jack before she leaves suggests that she really is Chuck's mother.
In the episode Inglourious Bassterds, Jack says he will give back the hotel to Chuck under one condition: he wants to have sex with Blair, so that Jack could have everything that Chuck has ever wanted. Jack follows Blair to a boutique and makes his offer. After Chuck makes it clear to her that Jack will never give back the Empire, and is going to sell it off to someone else, she decides that she has to sleep with Jack to save Chuck's hotel. Blair goes to Chuck's old apartment to meet Jack, wearing the dress Jack sent her, and tells her that her one condition is that he sign a contract stating that he will never tell Chuck what happened and that he will sell the Empire back to him so he's not suspicious. Jack kisses Blair, and then tells her that Chuck did know and that he knew that Blair would want to do whatever it takes to help him. Hurt and disgusted, Blair cries and tells Chuck that she can't believe he would do this to him, but Chuck tells her that she was the one who cheated on him, despite the fact that he orchestrated it. She breaks up with him and goes home.
In the episode The Unblairable Lightness of Being, Chuck is desperately trying to get Blair back and apologizes to her. While Blair really wants for them to get back together, she refuses because of the disgust she feels for still loving him even after the way he acted. Blair feels it is not right to go as far as she did to help a person, no matter how much you love them; considering what she did for Chuck, she couldn't live with herself if she stayed with him. Chuck begged Blair to stay with him, and to not end their relationship, saying 'We have to see this through until the end', but Blair replies with 'This is the end' and thus ultimately ending the relationship, causing him to go back to seducing any woman he desired, only to get over how devastated he is.
In the episode Dr. Estrangeloved, Chuck wants his best friend Nate back, which would be easier without him dating Serena. Chuck also tells Nate that he is devastated about his and Blair break up and he need a friend right now. In order to break up Serena and Nate, Chuck enlists the help of Jenny, who has been after Nate ever since her breakup with Damien. He gives her ideas on how to drive them apart, finally inviting Jenny to go out drinking with him and Nate and dropping subtle comments about how grown up and hot Jenny is to get the idea in Nate's mind. However, Nate eventually realizes what Jenny is doing and orders her to leave after Serena shows up at his apartment to apologize.
In the episode It's a Dad, Dad, Dad, Dad World, Chuck avoids Lily after finding out there was a possibility she had cancer, because after losing Bart and being betrayed by Elizabeth, he couldn't stand losing Lily too. Blair goes to talk to him, telling him he shouldn't close his heart to Lily. Chuck then goes to see Lily at the gala and tells her he's sorry for being so absent and that he will stay by her side the entire time she would go through this. He is suspicious of how healthy Lily looks despite being diagnosed with a cancer relapse, and enlists Jenny's help in finding out what Dr. van der Woodsen is hiding. Later in the episode, Blair learns that she has been accepted to Columbia thanks to Chuck, who sent in an application for her when they were still together after joking about it with Nate. He knew that she was too proud to admit being at NYU was a mistake, and wanted her to be in a school where she belonged.In the episode Ex-Husbands and Wives Chuck and Jenny are trying to figure out what's wrong with Lily's medication, after accidentally learning that what Lily was told was oxycodone was actually an antibiotic. They ask for Blair's help, but she turns them down due to her dislike of Jenny. On their own, they go to check out the prescribing physician, Dr. Campbell's background and find out that she's a psychiatrist. They run into Blair, Dan, Nate and Cameron at her office, who were led there because a woman named Holland had accused Rufus of cheating on Lily with her; they all eventually realize that Holland and Dr. Campbell are the same person. Putting their heads together, they figure out that Dr. William van de Woodsen, Serena and Eric's father, and Dr. Holland Campbell have been working together to make Lily believe that she has cancer in order for him to get closer to Lily; the antibiotics mimic the symptoms of the cancer she is supposed to have. Later that evening, Chuck and Blair have to find some way to stall Holland, so they do what they do best: role play. Acting like a couple they spill out all their relationship issues, from Blair sleeping with Jack to Chuck selling Blair out for his hotel. But when Dan signals to them, they accuse her of prescribing medicine to Lily. When they return to the Van Der Woodsen's apartment to find William, he is gone. Chuck waits with Blair for Cameron to come pick her up and tells her that he will be waiting for her at the top of the Empire State Building at 7pm and if she isn't there by 7:01, he is closing his heart to her forever. In the season finale Last Tango, Then Paris, Blair spends the day trying to avoid meeting with Chuck, but ultimatly decides to meet Chuck and continue their relationship after Dorota gives birth to her baby and encourages Blair to go with her heart. Because she stayed at the hospital with Dorota too long, she is late meeting Chuck and finds the peonies he had bought for her in the garbage can. Chuck believes that Blair is over him and, devastated, sleeps with a lonely Jenny Humphrey, who finally loses her virginity. After this, Blair visits Chuck and nearly walks in on Jenny, but Jenny leaves quickly and is not seen. Blair tells Chuck she loves him and the rest doesn't matter. Chuck is thrilled to hear this and then decides to propose to Blair the next day. As he is midway through his proposal, Dan attacks Chuck in his anger over Chuck sleeping with his sister. Blair realizes what Chuck has done and tells him to "forget this night ever happened" and walks out on him. A week later, Chuck is seen wandering through an alley in Prague. He is mugged by two men. They find the engagement ring that was supposed to be Blair's, but Chuck does not want to give it up, telling them he has money to give and that he is rich, but he has to keep the ring. As he tries to take back the ring, Chuck is shot in the back by one of the men. The last shot is of him left bleeding in the alleyway. Whether he lives or dies is unknown. Eva (Clemence Poesy) who has no idea of his wealth or of who he is. He creates a fake name and persona, Henry Prince, as he no longer wants to be the manipulating Chuck Bass. He eventually reveals who he really is and returns to New York with her at the request of Blair and Serena. Blair insists she no longer loves him, but still schemes to undermine his new relationship. He eventually falls for one of her schemes and breaks up with Eva. He realizes his mistake and begs her to take him back, but she refuses, saying that he showed his true feelings by continuing to believe Blair over anyone else. Chuck then declares war on Blair and sabotages various aspects of her life by making her lose a teacher assistantship, inviting Jenny Humphrey back to town to undermine her power over her "minions", and generally trying to make her miserable. They soon reach a hesitant truce, after Jenny tells them that their hatred of each other and the subsequent games that they play will assue the mutual destruction of their lives.
In the seventh episode of fourth season, Nate and Serena wants to be sure that the war between Chuck and Blair is over, for good. That's why they want them to sign a "real treaty", with provisions for every possible interaction they could have. Nate and Serena vow to never be friends with them ever again if either one of them breaks the treaty, and it seems that the two have reached a semi-stable phase of friendship.
Dan Humphrey, upset that Jenny is too afraid of Blair to return to the city for Rufus and Lily's first anniversary party, sends a blast to Gossip Girl stating that Jack Bass and Blair had another fling in south of France over the summer in an attempt to convince Chuck to give Jenny amnesty for the party. He goes to see Chuck to sympathize with him about Blair's betrayal, but Blair appears and both of them tell him that they don't believe the blast, telling him that they had suspicions that someone would try to take advantage of their truce. Blair explains that Jack was in Chile over the summer, which is why they knew the blast was fake; Chuck is suspicious as to how Blair knows this information, but doesn't get a chance to inquire further.
At Blair's twentieth birthday party, Chuck asks Blair again that how she knew where Jack was. When she still doesn't answer, we see that Chuck get's little bit jeolous. Dan leaks a video that was a secret provision of Chuck and Blair's treaty. In that video, she is drunk and singing "Stand By Your Man" at an after-party for singer Robyn's concert in Switzerland when she was still with Chuck. She feels verry embarassed. She thinks Chuck leaked it because he is suspicious that she and Jack really did get together over the summer, since she knew his whereabouts. Blair angrily reveals to him that she hired a PI to find Chuck over the summer, but the only Bass she could find his uncle.
At the end of the party, Chuck appears. He wants to let Blair know that the treaty is over after what happened that night. They express their hatred for each other and Chuck rips up the treaty. It looks for a moment as though Chuck is going to physically hurt Blair, but they instead have "hate sex" on top of her piano. This leads to a multi-episode secret affair, starting out in an angry way, but slowly turning into a more romantic relationship.In the The Witches of Bushwick, Chuck accidentally tells Blair that he loves her during sex, and, after a brief pause, Blair decides to brush it off and they continue their lovemaking; though, Blair has no idea that, that it is how he actually feels. Although Chuck and Blair spend the episode striving for different ends which will eventually alienate each other (Blair to become the face of Anne Archibald's charity, Girls Inc, and Chuck to increase the revenue of The Empire by returning to his bad boy persona, the defining feature of his brand), Blair makes the decision to attend Chuck's Saints and Sinners party in order to confront him. Chuck confesses that he loves her, and Blair tell's that she feels the same way. This makes them kiss in front of everyone after the curtain concealing them is pulled down. Anne tells Blair that she can no longer be a part of Girls Inc just as Chuck's publicist KC tells Chuck that she thinks Blair will be good for business. Blair re-thinks her decision to sacrifice it all for their relationship, and she and Chuck break up once again, because Blair wants to find herself and establish a career of her own so she doesn't succumb to being only "Chuck Bass' girlfriend". Chuck promises he'll wait for her, and both affirm their belief that their love will reunite them in the end. On Thanksgiving, Chuck and Blair run into each other at Serena's house, Chuck offers to leave but she tells him that she was heading to JFK anyway and came to drop off the traditional pie and that they should get used to this. They hear about Serena being hospitalized and while they're sharing that maybe nothing can change between them, Jenny walks in and their conversation interrupts. While driving Blair home, Chuck tells her that he showed up only for Serena when she told him that what happened with Serena made her question what she told him after the Saints & Sinners party. Chuck tells her that he cannot be her friend now as much as he wishes he could. But even after that Blair still sends him her traditional pie saying that 'Even though we can't be friends, doesn't mean that we aren't.'
Chuck begins dating Raina Thorpe, daughter of buisnessman and enemy of Bart Bass, Russell Thorpe, in hopes of making Russell buy the Bass Industries and then give it back to him. Raina and Chucks relationship turns to a more serious kind of relationship and is no longer about buisness. Blair finds out about them and she's hurt. Russell Thorpe asks Chuck to kick Lily off the board of Bass Industries to prove his loyalties to him. Chuck does all that Russell requests in order to win back Bass Industries, but Russell only wants revenge for Bart's part in the ending of Russell's relationship with Lily. Chuck tries to make Raina a surprise by creating a dinner that reminds her of Venice, as Raina had missed her flight. Raina and Chuck are in the middle of a conversation when Lily comes into the room and asks Chuck why he kicked her off the board of Bass Industries. Lily and Chuck have an argument and Raina yells at Chuck after hearing and seeing what he was doing to Lily, because loyalty to family is extremely important to her. Raina storms out the room, but Chuck tries pulls her back in and tries to have a conversatioin with her about what happened. Raina tells Chuck that family doesn't matter to him and that what he's done to Lily is wrong. Raina then goes on to say that she actually cares about her family, and that she wants to end their relationship.
Chuck tries to win Raina back by sending Nate to convince her what a good guy he is, but Raina develops feelings for Nate instead, and they have a short lived relationship; this is awkward for Chuck at first, but he eventually gets over it.
Chuck is finally back to wanting Blair, but he cant connect with her because Blair is ignoring him. Chuck does not know why Blair is acting strangely towards him, so he convinces Blairs old boss from W to ask Blair herself to help her with a photoshoot as a favor. Blair accepts and Chuck does his own investigation. Blairs old boss finds out that Blair had a life changing kiss and texts this to Chuck. Chuck finds himself in Brooklyn asking Dan if he knows anything. He tells Dan that Blair had a life changing kiss and that he needs to know who it was with. Dan seems surprised and defends Blair saying that Chuck should leave her alone. Chuck leaves, realizing that Dan was the one Blair kissed. He invites Dan to the photoshoot as well in an attempt to humiliate him in front of Blair. When Chuck confronts Blair about the kiss, she says that it was life changing, because it make her realize that she wanted it to be with Chuck. Later Blair tells him that now that she knows she's ready, she realizes that Chuck is not. She says that she's sorry and walks away.
After Russel Thorpe tell's Chuck that it was his father who started the fire where Raina's mother died, Chuck is confused and the only one he wants to talk is Blair but Blair has started to date Louis, Monaco's prince. When Chuck learns that Blair and Louis might get engaged, he get's again jeolous and get's drunk. He ruins their engagement party saying to Louis' mother Sophie that "Blair loves him and everyone else is just a waste of time." and is escorted away for there. Later when Blair is visiting Chuck at the empire, he says that he needs her and that only thing that has ever been real is them. Blair reveals that Louis has asked her to marry him, this revelation makes Chuck furious and he smashes a glass window right next to her face. This makes Blair run away. Blair also get's a cut to her face.
The next episode Jack comes to town and soon as Blair sees him, she goes to warn Chuck. Chuck is trying to get his mind of Blair and he works. Louis comes to see Chuck and notices Chuck's hand. Louis confords Blair saying that he saw Chuck's hand that it wasn't the ring that cut her face, it was Chuck. Blair says that he didn't tell him because she didn't want embarrass Chuck.
Jack comes to see Chuck and asks him that how does it feel like when the love of his life is leaving him for a prince. This makes Chuck angry anh he hits Jack and Chuck is escorted away again. When Chuck and Jack discover the truth that it was actually Russell Thorpe, who started the fire, they work together to make Russell to leave town. Nate also tell's Raina the truth and this makes her convinsed that her father is a bad guy. To make Chuck pay for turning Raina against him, Russell contact Blair saying that Chuck needs help and he lures her to Chuck's unfinished hotel. At the same time, Chuck goes to Louis' and Blair's party to win Blair back.
In the season 4 finale, picks up right after Russell lured Blair to Chuck's new hotel and traps her in a room. She manages to secretly call Chuck (who is still on her speed dial) so that he can hear what is going on and discover where she is. Chuck, Nate and Raina come to the hotel and Chuck rescues Blair from Russell. Raina confords her father and Russell is send to prison.
After when Blair is rescued, Chuck says to Blair that he's sorry for everything and asks to buy her a drink to calm her nerves, before he can take her back to Louis. Blair and Chuck goes to bar mitzvah party and begin dancing and smiling. Louis is still waiting for Blair at the party. His mother arrives and suggests that Blair isn't coming - he needs to give up. Louis insists that Blair will be there.
However, back at the bar mitzvah, Blair suddenly realize that she and Chuck still have chemistry so she pulls Chuck into another room and the two start kissing and have sex. Chuck and Blair head to the party and Blair admits that she will have to tell Louis that it's over. Chuck asks if she loves Louis, and Blair says she does, but not like she loves Chuck. She explains that with Louis, her love is lighter, more simple and makes her happy, but with Chuck it's intense and all-consuming. She expects that Louis will have left Constance by now as she has been so long. Chuck tells her to drop him off at Constance and then take the limo to the consulate. When they get to Constance, Chuck is surprised to find Louis still waiting. Louis says that he believes in Blair and knows she will figure it out and arrive. At that moment, Blair appears as Chuck left his jacket. She turns to Louis and says they need to talk, but Chuck interrupts and says the pair have his blessing and he is pleased they are getting married. Later, Blair finds Chuck and asks him why he did that. He explains that she deserves to be happy and says there is a difference between "great love" and the "right love". He points out that at the Empire State Building he didn't wait for Blair, but Louis waited for her all night. He asks how she feels about the night, and when Blair admits that she feels terrible, Chuck tells her that she is feeling guilty. He admits that he feels guilty too and suggests he is growing up. Blair says she didn't want to give Chuck up yet but he kisses her on the forehead and announces that she is the most powerful woman he knows. He says they need to let each other go and the pair tell each other: "I will always love you."
Some time later, at the Van Der Woodsen apartment, Blair is preparing to spend the summer with Louis in Monaco, but is civil when she says goodbye to Chuck. When Nate and Chuck return home, Nate sees that Chuck is really hurting over Blair and Chuck admits that Blair shine's when she is with Louis, whereas he just brings out her dark side. He says she should be with Louis. Nate asks Chuck does he still love Blair and Chuck answers that he does. Nate is impressed that he is maturing and suggests that they spend a "lost summer" together. He spins a globe and tells Chuck to point at a location. Chuck smiles when they discover where they will be travelling to.
The episode ends with Dorota cleaning up after Serena and Blair have left for the summer. She empties the trash in the bathroom - without realising that there is a positive pregnancy test in it.
Chuck met a actress/stuntwoman, Zoe Bell, over the summer as he struggles to get over Blair. 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. Blair finds out that she's pregnant, but she isn't sure if the father is Chuck or Louis. She takes a pregnancy 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 Chucks.
Chuck starts to see a therapist about his numbness, learning that it is a psychosomatic response to his emotional pain. Dan, who worried about Chuck when he paid people to assault him, starts to become a close friend of Chuck's, and buys him a dog. At first Chuck doesn't like the idea of a pet, but later keeps the dog and names him Monkey, a reference to the Gossip Girl book series.
Later, we see that Chuck is trying to be a better person. 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 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.
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 blaming Chuck for his dark side and she's now sure that she was the one that brought out that side in him. 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.
In the episode "Riding in Town Cars with Boys" Chuck and Blair finally decide to get back together and make plans to run away, but get into a serious car accident. Blair wakes up, having lost the baby, but Chuck is in a coma due to massive blood loss. Blair then makes a pact with God, where she promises to stay with Louis if God will save Chuck's life. Moments later, Chuck awakens and asks for Blair. After they get out of the hospital, Blair focuses on her wedding with Louis. Chuck is upset and confused by Blair's avoidance of him Louis is sure that Blair is having an affair with someone, and considers hiring a private investigator when he realizes it isn't Chuck. After Chuck sees Blair and Dan entering a building that only Blair has the key for, he believes they are having an affair, and tells Louis about it. Later we find out that Blair has been going the church with Dan, to keep up her pact with God after she believes that God saved her life.
During the wedding in the bridal suite, after Eleanor Waldorf understands that Blair isn't going to be happy with Louis, she convinces Chuck to talk with Blair so she doesn't make a terrible mistake. Blair reveals to Chuck she loves him more and more every day, "if it's even possible to love someone that much". Someone (later revealed to be Dan) releases the tape of this conversation to Gossip Girl, which stops the wedding. Before the wedding, Serena tells Chuck about Blair's pact with God. Chuck confronts Blair, who believes he was the one who sent the tape. Louis comes to the room and Blair apologizes, and they continue the wedding. As Blair and Louis are dancing their first dance at a wedded couple, Louis tells Blair that he only married her to keep up appearances, and that while she must smile and pretend they have a perfect marriage, in reality their union is only for show and he has no feelings for her anymore. After realizing the mistake she has made in marrying Louis, Blair leaves her own wedding with Dan to flee to the Dominican Republic to seek an annulment before the Grimaldis can form a counterattack, but don't make it because Blair didn't have her passport. She and Dan get a hotel room, where Chuck and Serena finally find them. Chuck tells Blair that he loves her and he will protect Blair from the Grimaldis. Blair chooses to give up and wait out the the conditions of their pre-nuptual agreement: Blair must remain married to Louis for one year, or must pay the dowry that the Grimaldis waived before the wedding.
Later, we find out that Chuck paid Blair dowry, which almost bankrupted Bass Industries, because he wanted Blair to be free to be with whomever she wanted, whether that person was Chuck or not.
In the episode "The Princess Dowry" Blair reveals that she loves Chuck but isn't in love with him right now. Chuck finds out that Dan releases the tape in Blair wedding causing Blair to blame him for releasing it. This makes Chuck very furious, and he starts to question his friendship with Dan.
After Blair's divorce is finalized, Chuck learns that Blair started to date Dan, and this makes Chuck very upset and hurt.
Blair and Chuck come together again in the episode "Raiders of the Lost Art", when Chuck asks Blair help to find out what Diana Payne is hiding and why she's pretending to be his mother. Blair helps him, and we finds out that Chuck's father Bart is actually alive, and that he faked his death because someone was after him and threatened their entire family. It is later revealed that that person is Andrew Tyler, the Bass' private investigator; his threat to the Bass family is destroyed after a scheme that Chuck and Blair designed catches him, allowing Bart to come out of hiding for good.
Blair starts to spend more and more time with Chuck, which makes Dan jealous. Dan invites Blair with him to Rome for the summer, where he will be doing an internship. Blair accepts, but we see she isn't quite happy in her decision. After Gossip Girl start to post excerpts from Blair's diary from a year ago where Blair wrote, "I will never forgive Chuck what he did that night, he's a monster and he deserves to be alone." Blair goes to see Chuck at the Empire, because she wants to know that Chuck isn't hurt. Chuck tells her that the blast doesn't matter, because it was a year ago, and that they have been through so much since then and made amends. Chuck asks her if she is still with Dan, and when he finds out that she is, he tells her that he's tired of this game and that he needs to move on.
At the Empire, Bart is questioning Chuck about his relationship with Blair. He says that he made a lot of mistakes when Bart left, including ruining things with Blair. Bart encourages Chuck to win Blair back and gives him the engagement ring that Chuck was about to give to Blair in season 3.
Later Chuck arranges a meeting where Chuck's father announces that from now on, he will be the only CEO of Bass Industries, leaving Chuck and Jack out of the company. At the same time, Blair makes her choice and chooses Chuck instead of Dan.
Blair confesses her feelings for Chuck saying, that she loves Chuck and despite trying desperately to kill those feelings, she can't and wants to be with him. Chuck rejects Blair out of anger from losing the Empire, using the same reasoning Blair used at the end of Season Four: he doesn't want to be "Blair Waldorf's boyfriend", he wants to be Chuck Bass.
In the end of the season 5 finale, Chuck goes to see Jack Bass, so they can work together to take down Bart Bass and take back Bass Industries. They go to a casino in Monte Carlo and play black jack, where Jack is counting cards and they plan their next move.
Later, Blair comes to the casino and joins the game to win Chuck back, stating that he has been pursuing her for years, and now it's her turn to chase him. She puts in all her chips and says that she's all in, and asks Chuck if he is too, gazing at him intently.
We learn in the first episode of Season 6 that Chuck and Blair spend couple of nights in Monte Carlo together. They promised to be together after they solved their own things (Chuck is trying to discover his father's secret and is trying to get the empire back). When Blair and Chuck meet again in Upper East Side, Blair tells Chuck that she's still "All in" and Chuck responds "And my bet's on us" We also find out that there is a ring involve that is hanging in Blair neck. Chuck is trying to find out Bart's secret, so he meets up with Bart's former translator Amira to find out why Bart really faked his death four years ago (in Season 2). At the end of the episode 1, Amira tells Chuck that Bart was willing to pay her 10 million dollars to leave the country because she knows something about Bart's past.
In episode 2, Bart sends a text from Blair phone to Chuck's phone to distract Chuck, so he can make Amira leave town. Chuck and Bart have a talk where Bart asks Chuck that he has to stop this childish nonsense, Chuck responds that Bart has taken everything from him and now is the time to take everything from Bart. In the end of the episode 2, Amira sends to letter to Chuck containing a picture of her, Bart and mysterious man and the note that Chuck can't contact her again.
In the third episode in Season 6, Chuck comes to Blair's rescue when she is in trouble with her fashion show. Chuck also finds the mysterious man, who is Bart's former bodyguard. In the end of the episode, Chuck comes to Blair house to celebrate with the Bottle of Dom and tells her that he found the mystery man in Amira's photo named Dave, who drove Bart to meet someone called Lady Alexander. He also tells Blair that if they help other, they can be together sooner.
In the next episode, Chuck and Blair are trying to find Lady Alexander. After they visit the studio of Brian Batt, they find out that Lady Alexander is a horse. Bart Bass bought Lady Alexander and many other expensive horses from the man named Sheikh Hassan. Blair find out that there is a three day house show just outside of town and maybe there they will find some answers.
Unfortunately, Sheikh is already dead but his daughter is there with the one of the horses. Sheikh's daughter Amin tells that Bart bought many horses and that Bart told her that the horses went to some farm in Virginia. Chuck finds out that Amin is friends with Bart and she calls him "Uncle Bart".
It's not until Blair convinces Amin that Chuck is the good guy here and asks her to look up that where the horses that Bart bought really went.
Bart comes to the horse show and asking Chuck again to stop what ever his doing. At the end of the episode, Amin comes to Chuck's hotel room and tells that she knows that the horses that Bart bought didn't went to any farm. Chuck is convinced that the horses were just covering up something else.
Amin tells that the Sheikh's family have a oil business and that Bart could not be including that because if he had, he would have been breaking the law. Now Chuck is convinced that he knows Bart's secret. Chuck calls Blair and tell's her everything and all he needs now is proof.
In the episode "Monstrous Ball" Chuck is trying to get Lily on his side with his battle with his father but he fails and says to Blair that "Bart has Lily wrapped around his finger."
When everybody finds out that Serena and Dan slept together when Dan and Blair were still together, Blair yells at them and goes to Chuck's place and thank's Chuck for never sleeping with Serena.
Chuck says to Blair that he always feared that Dan was better man for her but Blair responds that no-one is better for her than Chuck is. Blair tells Chuck that she will wait for him as long as it takes, if that is what he wants and Chuck says that good thing comes to those who wait. They almost kiss but they are interrupted by Blair's phone. She kisses him on the cheek and leaves.
In the next few episodes, Chuck learn that there is a evidence about the oil deals behind one of Bart's paintings. He learns that Lily has them and is trying to make Lily see that Bart is evil. Lily doesn't believe Chuck and burns the evidence. This causes Chuck to push Blair away saying that they can't be together anymore. Chuck starts to spin out of control, but Blair comes to his rescue.
In a thanksgiving dinner hosted by Serena and Dan, Chuck finaly turn Lily against Bart and Chuck tells Blair that Lily will help them to take down Bart and asks Blair to go to war with him. She accepts.
In "The Revengers" Bart threatens Blairs safety and forces Chuck leave the city for Moscow and to never come back. Chuck and Blair have a emotional farewell in the airport. Chuck gets on the plane and later that night at Bart's party it is revealed Chuck's plane crashed with no communication, and Chuck is presumed dead. Blair is devestated about the news. Luckily, Chuck shows up to Bart's party and reveals to the guests that this own father tried to kill him. In 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 three times and calls him "a boy". Bart is about to attack Chuck but he moves out the the way and Bart falls from the roof. Bart hangs a while on the edge. Chuck refuses to help him saying that everything he says is a lie. Bart falls to his death with only Chuck and Blair as witneses, They run away from the scene and screen says "To be continued"
The finale episode starts right where "The Revengers" ended. Chuck and Blair try to figure out how can they get out of the Man of the Year party. Blair calls to Georgina and asks her to look for Arthur, Chuck's limo driver. She finds him and Chuck and Blair hide the to the car's trunk to avoid the police. Arthur drives them out of town to some hotel.
The next morning someone knocks on the door, it's Jack Bass who's there to help. Jack tell's them that he knew where they where because he has a tracing device in Chuck's limo from the back of a day when he hated Chuck and he though it was a little odd when Chuck's limo driver drove out of town in the middle of the night. Jack asks Chuck did he kill Bart but Chuck says that no, it was selfdefence, and the only one who saw Chuck and Bart on that roof was Blair because Bart had turn the roof camera's off. Blair also convinces that she's not gonna tell anyone that she saw him there with Bart "even if they torture her".
Jack says that there is another way to solve the situation, Marrige. Jack tell's them that "spousel situation" means that a wife cannot be forced to testify against her husband. First Chuck is against but when Blair remind him that in Season two, Chuck said to Blair that if they got together, they would be boring and they clearly aren't that now. Chuck says that he was a stupid child when he said that and a life with Blair can never be boring. Chuck takes the ring from Blair neck and asks her "Blair Cornelia Waldorf, will you marry me?" Blair says yes, puts the ring to her finger and they kiss.
When Chuck and Blair are in a court house trying to get married, Chuck says to Blair that he doesn't want to start their life this way and that Blair needs to be surrounded with the people she loves. Chuck calls everyboby to come to the Central Park and he and Blair announce to everybody that they will get married. Two little girls spots them and they call the police.
The wedding takes place in Bethesda Fountain in Central Park. When Cyrus is reading a poem, everybody hears a distant police siren. Blair asks if he can go a little faster, Chuck says that maybe they can skip to the "I Do" part. Cyrus announds that Chuck can kiss her bride, They do a hollywood kiss. Chuck whispers to Blair that he loves her. Three police men come and ask Chuck and Blair to come with them. Chuck and Blair get out of the police station because the police has no real evidence that Chuck even was in that roof and only one who knew is now his wife. Everybody gathers to Waldorfs and are about to have a wedding reception. When everybody found out that Dan was gossip girl, Blair gets furious but Chuck calms her down. Dan tell's them that gossip girl is dead and now they can really move on. Next this we see is five years later, Chuck and Blair are still happily married and they now have a son named Henry.
Gossip girl end with Chuck and Blair holding hands as they watch Serena and Dan get married in their house.
Appearance and StyleChuck has the irresistible look that his family's money has given him. Women, and even a few men, can hardly resist him. He has dark brown hair and dark chocolate eyes. His hair is always perfectly styled, his skin has a natural tan, and he is always well dressed, often wearing stylish, colorful, well-tailored suits. Chuck is acknowledged as a fashion icon for men's wear, and is known for wearing a lot of purple in his outfits, his favorite color (because his father loathes it).
Chuck is very sleazy, self centered, and has a horny sense of humor. However, he is also shown to be very loyal to the select few he deems worthy,such as offering a loan for Nate and Anne Archidbald in season 2 and Blair's dowry in season 5. Throughout the first season he displayed a variety of near-sociopathic tendancies including attempted rape (on two young girls) but in later seasons has matured into a respectable young adult. He is extravagant and often times throws around money but it seems to come from deeply rooted insecurities which were most likely instilled by his demanding father. He is also very witty and quick to verbally spar, showing that he is quite intelligent. His narcissism is apparent, often quoting "I'm Chuck Bass" after someone ask's him a question on why he is deserving of such things (e.g Ivy league education).
He started to change due to Blair's influence and then later his relationship with Eva. Finally he changed even more when Blair left him. Chuck started seeing a therapist and he's starting to change into a new, better Chuck Bass.
- Bartholomew Bass (father)
- Misty Bass (mother)
- Donald Bass (younger brother)
- Donetella Contessa (fling)
- Tiphany (fling)
- Jenny Humphrey (one night stand)
- Kati Farkas (fling)
- Katie Soave (fling)
- Vanessa Abrams (one night stand)
- Blair Waldorf (wife)
- Georgina Sparks (lost his virginity to her)
- Greg (ex-boyfriend)
Relationships (TV Series)
- Bartholomew Bass (father)
- Elizabeth Fisher/Evelyn Bass (mother)
- Lily Bass (step-mother)
- Jack Bass (uncle)
- Monkey (dog/pet)
- Blair Waldorf Bass (Wife)
- Henry Bass (Son)
- Blair Waldorf Bass (wife)
- Jenny Humphrey (one night stand)
- Vanessa Abrams (one night stand)
- Georgina Sparks (lost his virginity to her)
- Eva Coupeau (ex-girlfriend)
- Raina Thorpe (ex-girlfriend)
- Ashley Hinshaw (one night stand)
- Josh Ellis (kiss)
Chuck: I'm Chuck Bass.
Chuck: Look, Nathaniel, I care about three things: money, the pleasure money brings me, and you.
Blair: Don't worry, I can be bitch enough for both of us. Chuck: I've still got the scars on my back to prove it. (Blair pushes him out the door) You know, they say if you love something, you should set it free. Blair: Ugh! They say when you hate something, you should slam the door in its face! Chuck: I love it when you talk dirty, Blair. (Blair slams the door in his face)
Chuck (to Nate) : Look, I know you hate me. I was in love with Blair and I'm sorry, we do not have time to argue about this.
Chuck(to Blair): Let’s take it slow this time. Do it right.
Blair: Chuck Bass is a romantic, who knew?
Chuck: Now you do, and it’s all that matters.
Chuck: Just because we can't say it doesn't mean it isn't true.
Blair: 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.
Serena: Chuck, why did you just do that?
Chuck: Because I love her. And I can't make her happy...
Blair: What do we have, Chuck?
Chuck: Tonight. So shut up. And dance with me.
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? There's a future I never imagined. Blair: With good reason.
Blair: Chuck Bass, I do believe all your years of under-age boozing and womanizing have finally paid off. Truly, I am proud. Chuck: And you are my toughest critic.
Chuck: Victory party, here, tomorrow night. Blair: I wouldn't miss it.
Chuck: 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: That's it? Chuck: I love you too.
Blair: We need to talk. Chuck: I prefer to talk after.
Chuck: We could never be boring. Blair: You say that, but I know you. You're Chuck Bass. Chuck: I'm not Chuck Bass without you.
Chuck(to Blair): If you wanted to play rough, all you had to do was ask.
Chuck: I am so sorry for the pain I've caused you. And I know I can't take it back, but I want to try and make it up to you. Even if it takes me the rest of my life.
Blair: Are you upset because you kissed a guy? Chuck: I'm upset because I kissed somebody that wasn't you.
Chuck: Judge away. Shame turns me on.
Chuck: Well, let's catch up, take our clothes off, stare at each other.
Chuck( to Blair): Well, you look ravishing. If I were your man, I wouldn't need clues to find you.
Blair: I'm sorry, but I have to be Blair Waldorf first 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.
Nate: Still love her? Chuck: Can't imagine the day I won't.
Chuck: I'm Chuck Bass, the love of her (Blair) life. Anyone else is just a waste of time.
Chuck: Don't mock the scarf Nathaniel. It's a signature.
Chuck (to Blair): I'm sorry for losing my temper the night you told me Louis proposed to you. I'm sorry for not waiting longer at the Empire State Building. I'm sorry for treating you like property. I'm sorry I didn't tell you I loved you when I knew I did. Most of all, I'm sorry I gave up on us and you never did.
Chuck: Because I'm Chuck Bass and you're Blair Waldorf. And I love you.
Chuck: Just because Louis is the father of your baby does not mean you should be with him,you should be with me. Blair: Why? Chuck: Because I'm going to love your baby as much I love you.
Chuck: I just wanted you to be free. Whom you choose to love with that freedom is up to you.
Chuck: Don't marry him. Blair: Chuck ! Chuck: Don't marry him. Blair: All those people downstairs waiting for me. Chuck: Yes they are. But they also want you to be happy which you're not going to be if you go through with this. Tell me I'm wrong and I'll leave. You can't. Because it should be us up there and you know it. Blair: It isn't that simple. Chuck: It's only that simple you told me you loved me, I know it was true. Blair: It is ! Of course I love you Chuck I've always loved you. I love you more on more everyday if it's even possible to love someone that much.
Chuck: Serena, you accepted responsibility without hesitation for maybe the first time in your life. And Nate, you had more fun not being you than you've had actually being you. Which means you now know you need to change.
Serena: Is it just me, or is what he saying actually making sense?
Nate: Maybe we're not awake yet.
Serena: Have you ever thought about writing a book?
Chuck: People like me don't write books, they're written about.
- Charles is of Old German origin and its meaning is "free man". From "karl", similar to Old English "churl", meaning "man, serf". The first Holy Roman Emperor (seventh to eighth century) Charlemagne Magnus, meaning "Charles the Great" was a powerful German leader who created a more ordered society out of the chaos that followed the fall of Rome.
- Bartholomew is an English given name that derives from the Aramaic name meaning "son of Tholmai". "Bar" means "son of" in Aramaic and thus its occurrence in a personal name indicates a patronymic. "Tholmai" is commonly supposed to mean "furrows" and Bartholomew is accordingly read as "son of the furrows", meaning one who is rich in land.
- Bass is both English and occasionally Scottish. In the first instance it may have Olde English pre 7th century origins or it maybe French and as such was introduced by the Normans after the 1066 Invasion. Taking the latter first as this is the most satisfactory explanation, the derivation is from the French word 'basse' meaning somebody who was both broad and thickset. This word itself is a development of the Latin "bassus", meaning wide, as opposed to tall.
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