They ask for Blair's help, but she turns them down due to her dislike of Jenny. 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). In the following episodes Chuck returns to the Upper East Side with revenge for Lily. He is annoying to Serena, particularly because he smokes marijuana in her bathroom. 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 associaties with sordid stories from his past. In the final episode of season 2, Chuck admits to Blair his true feelings and the two finally begin a relationship. He is married to Blair Waldorf, the love of his life and is best friends with Nate Archibald. While mulling over her options at classmate Hazel's house, she comes across her mother's closet which is filled with lavish gowns. 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. 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. The next day Blair goes to confessional at church and admits that she is guilty about both her performance at Victrola and night with Chuck in the limo. They are all gathered at the Bass house for Dan and Serena's wedding. 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 eventually realise that Holland and Dr. Campbell are the same person. 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. 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.
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.
This begins their secret love affair.At the debutante ball Chuck starts to worry that he will lose Blair to Nate again. She rejects his advances and storms out on him, and he isn't seen to have any physical attraction to her after that. 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. 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. However, his uncle Jack sets Chuck up so the board will see his partying ways, and so Jack wins the company. They profess their love for one another in Chuck's limo. 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. 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. 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.
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