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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 apologize and they fall asleep together. However, when Blair awakes, Chuck is gone from her bed, and just a note that apologizes 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 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 talkt to Blair. Instead she asks him to tell her how he really feels about her, in order to respond to Nate's proposition. She also asks him to let her go if he (Chuck) doesn't really love her, after what she starts to cry. He tells her it was just a game, and Blair walks away thanking him. Serena witnesses this conversation and when she questions him about it, Chuck tells her that he loves Blair but he told her it was a game because 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 in fact can make her happy and happier than Nate can.
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 reuni
te.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 apologize and they fall asleep together. However, when Blair awakes, Chuck is gone from her bed, and just a note that apologizes 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 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 talkt to Blair. Instead she asks him to tell her how he really feels about her, in order to respond to Nate's proposition. She also asks him to let her go if he (Chuck) doesn't really love her, after what she starts to cry. He tells her it was just a game, and Blair walks away thanking him. Serena witnesses this conversation and when she questions him about it, Chuck tells her that he loves Blair but he told her it was a game because 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 in fact can make her happy and happier than Nate can.
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 reuni
