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Charles Bartholomew Bass was born May 19, 1991, to the late Bartholomew "Bart" Bass, a self-made billionaire who owns the The New York Palace Hotel, where Chuck resides. Both of his parents are now deceased, as of "It's a Wonderful Lie," leaving Chuck with only his step-family, the van der Woodsens and uncle, Jack Bass. Chuck's mother's name is never revealed, it is rumored that her name was 'Evelyn', but it has never been confirmed.Chuck attends the prestigious St. Jude's School for Boys with long-time best friend Nate Archibald. He is the resident bad boy of the Upper East Side, originally portrayed as a Casanova type. After sleeping with Blair Waldorf in "Victor, Victrola", he has taken on a softer side, and is often shown to be nearly monogamous in light of his love for Blair. He is the male version of Blair when it comes to manipulation and revenge, the two often coming together to form sometimes-elaborate plans for vengeance and self-gain. Fan favorites, they are often described as equals. In the second season, Chuck reveals to Dan Humphrey that his mother, Evelyn Bass, died giving birth to him. With the death of his father, Chuck essentially returned to his old ways before finally telling Blair that he loved her in the Season finale.
[edit] Season 1

Chuck grew up with Upper East Side elites Nate Archibald, Blair Waldorf, and Serena van der Woodsen. He is charming and very good looking. His father is Bart Bass, an entrepreneur, a successful businessman, who made a name for himself, rather than being born into money like Chuck’s friends’ parents. Chuck is often described as the bad boy of his circle, and although he can be manipulative, we learn that he has a sensitive and caring side to him, especially for those he cares about like his best friend Nate and love interest - Nate's ex-girlfriend - Blair Waldorf, who is the first girl he has ever loved and the first girl he admits to loving.

Chuck is notorious for being a playboy and is frequently shown sleeping with hired women for recreation. He also attempts to hook up with Serena and Jenny Humphrey in the pilot episode. Chuck was the only one who knew about Serena and Nate’s affair, but didn't tell anyone until after Serena came back, at the brunch his father was hosting. This behavior stops in season 3 when he finally tells Blair he loves her(season finale of season 2) and is finally with her as her boyfriend.

Chuck is shown as being fiercely loyal to his best friend, Nate Archibald. When Nate leaves Chuck's party angry and frustrated, Chuck winds up rescuing him from Carter Baizen and a risky poker game. He also said in a season one episode that the only things that matter to him are money, the pleasures money can buy him, and Nate.

However, Chuck unintentionally betrays Nate by sleeping with Nate's long-time girlfriend, Blair Waldorf, a few hours after they broke up. Chuck had always liked Blair but as she was Nate's girlfriend he had to stay away. Until then. Blair had come to Chuck for solace after the break-up, the two of them being close friends and oftentimes, partners in crime. Upon seeing Blair boldly perform a burlesque dance at Chuck's club Victrola immediately after breaking up with Nate, he becomes immediately smitten with her, and the two have sex in his limo on the ride home. It is clear that Chuck has a respect for Blair that he lacks when it comes to other women, thinking of her not only as his best friend's ex, but as a close friend herself. This is evident when before they have sex, he asks, "You sure?" to which she answers him with a kiss.

However, the morning after, Chuck finds her confessing at a Catholic church, and she tells him that they should never talk of what transpired between them, despite Chuck clearly not agreeing to this. At Blair's birthday party Chuck admits his feelings for her; that he cannot sleep for thinking about her and the presence of butterflies "fluttering" in his stomach. Blair isn't pleased with his sudden attention or amorous feelings, and just wants him to leave her alone. After Nate fails to reconcile with Blair on her birthday as she had hoped, Chuck consoles her and wins her over by giving her the $30,000 Erickson Beamon necklace she had put on hold that morning, expecting Nate to give it to her as her birthday present. They wind up having sex again, but unbeknownst to them, Serena spots them together. Serena later confronts Blair about this in "Blair Waldorf Must Pie", but Blair gets defensive and lies that her past two encounters with Chuck were simply "revenge sex".

Chuck and Blair carry on a secret relationship for two weeks, while Nate begins to reconsider his decision to break up with Blair. In Hi, Society, Nate expresses his newfound interest in Blair, who he feels has changed. Later, in the middle of a make-out session between Chuck and Blair in her room, Nate comes to visit her and asks her if the two of them can go to the debutante ball as friends. At first, Blair is reluctant, but caves when Nate shows her the heart pin she sewed on his sleeve before. As they prepare for the ball, Nate senses that Blair is not really interested in him and may be seeing someone else, so he asks Chuck to find out who the secret guy is. Meanwhile, Chuck starts to feel jealous and insecure and fears that Blair and Nate might reconcile. So he decides to kill two birds with one stone and snaps a photo of Carter Baizen leaving Blair's apartment after picking up his coat. He convinces Nate that Carter Baizen is Blair's new guy, and an enraged Nate attacks Carter at the ball getting himself kicked out in the process, just as Chuck had planned. However, Blair cottons onto Chuck's machinations and promptly finishes things before going to look for Nate. Chuck looks for Blair in a last-ditch effort to explain himself, and ends up seeing Blair going to bed with Nate. A heartbroken Chuck leaves New York to avoid the pain of seeing Blair and Nate together.

Nate and Chuck spend Christmas in Monaco, where Chuck blackmails Blair with their secret in order to keep her away from Nate. However, she eventually realizes that revealing their tryst would hurt him too, so she informs him that it's over. Seething with jealousy, Chuck retaliates by writing an anonymous text to Gossip Girl detailing that Blair has slept with two guys in one week. The news spreads quickly, which ruins Blair and comes back to haunt him. After seeing the Gossip Girl news about Blair, Nate asks Jenny if it is true, and Jenny, who overheard Serena telling Dan, tells him that Chuck slept with Blair. As a result, Nate and Chuck have an explosive fight outside the school and Nate ends their friendship. At the end of the day, a devastated Blair returns to Chuck, saying she has no one else. To her dismay, he rejects her rather cruelly and tries to remain loyal to an estranged Nate.

In the meantime, Chuck's father and Serena's mother have become engaged, causing them to become step siblings. His father ended up kicking him out of the apartment to live back in his suite after Bart and Lilly became engaged and moved in together. Chuck constantly annoys Serena, but takes a brotherly liking to Eric, Serena's little brother, looking out for him and talking to him about his sexuality.

When Serena's old friend Georgina Sparks returns, Chuck does his best to help his soon-to-be stepsister through the difficult time. He eventually teams up with ex-friend Nate and ex-lover Blair to save Serena and counter Georgina's evil. With help from Blair, Nate, and Chuck, Georgina is eventually turned in to her parents and sent to a bootcamp. Nate, Blair and Chuck are dubbed "The Non-Judging Breakfast Club."

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, upon realizing Chuck is actually in love with Blair, Nate gives his blessing. While giving his best man speech, Chuck sees Blair and puts down his notecards, instead talking about true love and perseverance, inspired by his complex relationship with her. While dancing with Blair, he apologizes for the terrible things he said to her in the past and tells her that she doesn't belong with Nate. She replies, "You don't belong with anyone" and they kiss. He vows that this time they will take it slow and do it right, showing a softer, more romantic side of him. The two seem to be going strong until the day that he and Blair are set to leave for Tuscany for summer vacation when his father talks to him about becoming a better man and changing because of his relationship with Blair. Now having second thoughts about spending the summer with Blair, he ditches her for their trip to Tuscany, saying he cannot make the flight, and offers a rose to Lily Van Der Woodsen's interior designer, Amelia. Blair, unaware of Chuck's intentions, believes that his father must be running late and Chuck will probably catch the next commercial flight.
[edit] Season 2

Season Two begins with Chuck's quest to try and win back his "true love", Blair Waldorf in the season premiere "Summer, Kind of Wonderful". Blair, however, reeling from the fact that he ditched her at the airport, has hooked up with a handsome, seemingly perfect Georgetown guy by the name of James, originally in an attempt to make Chuck jealous. Even though he immediately sees through her ruse, he is crushed when he spots Blair's heart pin on James's sleeve, and she succeeds. Chuck is suspicious of James and orders a background check on him.

At the posh White Party, Blair makes out with James in a blatant attempt to provoke Chuck, but James finally catches on and is devastated that he was being used. She admits that he bores her, but they later reconcile when James admits that his name is actually Marcus and he is a British lord, just as Chuck gets a call with this same information. Dazzled by this revelation, she decides to carry on their relationship, but Chuck tries to stop her and admits that the reason he abandoned her was out of the fear that she would see "him," implying that he was afraid to let her get too close. However, when Blair asks him to tell her that he loves her "Three Words. Eight letters. Say it and I'm yours.", Chuck is unable to say the words. Blair, obviously disappointed, decides to leave with Lord Marcus. Chuck, who is still very much in love with Blair regrets the mistakes he made and drowns his sorrows in alcohol.

Chuck agrees to let Dan Humphrey hang around him for an evening out of boredom, not knowing that Dan plans to use him to write a story. Later, Dan finds out that Chuck is actually love-starved for his father's attention after he witnesses a failed attempt of Chuck setting up a meeting with his father over the phone. The two then bond after Dan later stands up for him during a bar fight, and they wind up in a jail cell together where Chuck becomes soft for a moment and opens up to Dan about his father. Chuck believes his father hates him because Chuck's mother, his father's "beloved wife", died giving birth to him. When Chuck is bailed out of jail by his father's lawyer, he promises Dan he'll try to get him out, too. However, Chuck accidentally finds out that Dan was trying to get close just to use him for his writing. Enraged, he says to Dan he will regret messing with him and that he lied about his mother dying at his birth.

In "New Haven Can Wait", while everyone is visiting college, Chuck and Nate stop at Yale University. He hopes to run into the "Skull and Bones" group, who eventually kidnaps 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 because of his embezzling father). Instead of betraying his best friend, Chuck sends them to Dan, telling them he's Nate. The Skull and Bone's kidnap Dan, take off his clothes (except for underwear) and tie him to a statue. When Nate hears what he's done, Nate ends their friendship and befriends Dan, leaving Chuck alone.

In "O Brother Where Bart Thou" Chuck, maddened with grief and angry at Lily, his stepmother for cheating on his father, attends his fathers funeral with Blair and Nate holding him up in support, and while there he disowns the van der Woodsens and is rude to Lily when she tries to talk to him. Enraged, he leaves the wake to flee to a bar, but Blair follows him, telling him she loves him. Confused, Chuck leaves Blair alone on the street, only to go to her house the next day to apologise and they fall asleep together. However, when Blair awakes, Chuck is gone from her bed, and just a note that apologises to her remains. Chuck has fled to Thailand.

Chuck's Uncle Jack brings Chuck back from Bangkok, and Blair continually tries to help him get over his father's death, at one point even talking him down from the edge of a building. When his father's will is read, it is revealed that his father has left him the company. 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 ex-stepmother to get rid of Jack, and they come up with the perfect way - Lily must become his legal guardian. Chuck signs the papers while Jack becomes angered, and then he tries to rape Lily at the opera for adopting Chuck. However, Chuck gets there in time and punches his uncle. He decides to move back into his old home with Lily, Serena and Eric.

Chuck is jealous and hurt when Blair begins dating his best friend 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 (who turns out to be a con artist). Jealous Nate asks Blair to move in with him, but Blair doesn't accept, instead she asks Chuck to tell her how he really feels about her. He tells her it was just a game, and Blair runs away crying, but Chuck later tells his sister Serena that he does love Blair but he can't make her happy. However, at Prom, Chuck makes it possible for Blair to have her dream prom, and proves to himself that he can make her happy.

In the second season finale, it is revealed to everyone that Chuck slept with Vanessa and Blair slept with Chuck's uncle so that he would find Chuck and bring him back. Blair tries to explain to Chuck why she did it and that she loves him, but Chuck runs away, 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 reunite.
[edit] Season 3

Chuck and Blair continue their relationship. They play games all summer involving other women: Chuck seduces a girl at random and, before anything can actually happen, Blair appears and humiliates the girl. After the woman leaves, the pair "stay in".

At a polo match, Blair freaks out when she can't find Chuck and it's assumed that he's with Alexandra Richards, when really he's home alon with a headache. They have a conversation where Chuck states that they could never be boring and that he's not Chuck Bass without her. They kiss and make up.

Chuck ends up letting Serena, who has decided not to go to Brown after all, crash at his place instead. Only when Serena ends up letting it slip during one of his business meetings that he secretly wanted to turn a New York property into a club, they have a major falling-out. He calls her a 'train wreck' and she storms out. Chuck then tells Rufus that Serena flaked on Brown, out of concern.

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 is beginning to be immersed in his work now. 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 deomnstrate 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 for a college society. Uh oh.

Chuck & Blair have a bidding war for the photo at the auction until it's sold to Serena. Turns out 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. Daphne, the assistant, 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 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 missing her high school days since she feels unworthy at NYU and calls her out on it. Only 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 her to claim the role of queen. Chuck ends up bring Jenny as his date to the movie premiere of "Fleur", causing Blair to be humilated.

When Blair shows up at the premiere to let Jenny have it, Chuck confesses that it was all his idea. Chuck says 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 time. Also, he paid a photographer to take pictures of Blair at the premiere so that she would get her mojo back. Chuck also sends a gift to Blair asking for "one-on-one tutoring".