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. When Chuck learns that Blair and Louis might get engaged, he get's again jeolous and get's drunk. A couple of hours later, Nate fails to show up to the party, iA 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. I cannot really articulate this thought into words but I feel like there's a connection between that and his thinking that love is both weak and something that would hinder his successChuck growing up without a mother puts the whole "signing over the hotel" situation into perspective. I can understand him being certain that Blair is coming for him, wishful thinking or whatever, but not waiting a minute past 8:00 was both very in-character and completely arrogant.I'm hearing a lot of realistic solutions to easily-avoidable problems. Chuck ends up bringing Jenny as his date to the movie premiere of "Fleur", causing Blair to be temporarily humiliated.
He creates a fake name and persona, Henry Prince, as he no longer wants to be the manipulating Chuck Bass. Blair finds out about them and she's hurt. At the charity 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 alone with a headache. They have a coversation where Chuck states that they could never be boring and that he's not Chuck Bass without her. 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. She went through some extreme things on the show and was struggling with her self worth and fitting in for a long time. Jack is implied to have something to do with this. Chuck believes that Blair is over him and, devastated, sleeps with a lonely Jenny Humphrey, who finally loses her virginity.
Chuck tries to make Raina a surprise by creating a dinner that reminds her of Venice, as Raina had missed her flight. Blair challenges him, saying she would like to see him try. 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. WTF? 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.
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. The two then kiss and begin a relationship, but Chuck decides to "take it slow and do right this this", which shows Blair that he is a romantic at heart. Misery loves company? 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.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 then makes a pact with God, where she promises to stay with Louis if God will save Chuck's life. 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. Blair was very content with this game, until Serena causes her to question it, telling her that the "line between acting like the scorned woman, and actually being the scorned woman is a slippery slope", which causes Blair to reconsider. 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. 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. 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 back to town to undermine her power over her "minions", and generally trying to make her miserable.