Blair and Chuck begin to kiss 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. He's not a character that has a lot of layers.
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. He even has visions of his father, who berates Chuck for being soft and not having the keen business sense that he has. This begins their secret love affair.At the debutante ball Chuck starts to worry that he will lose Blair to Nate again. He creates a fake name and persona, Henry Prince, as he no longer wants to be the manipulating Chuck Bass. 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. After they visit the studio of Brian Batt, they find out that Lady Alexander is a horse.
Chuck insists that he isn't responsible for the package, but is given a warning by his father. 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 next morning someone knocks on the door, it's Jack Bass who's there to help.
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.
He cries in her arms and they fall asleep on Blair's bed. 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.
In the next episode, Chuck and Blair are talking again, though he is still cold towards her. When Chuck learns that Blair and Louis might get engaged, he get's again jeolous and get's drunk.
Chuck's plans get cancelled, so he shows up at the dinner and gets a little too much info from one of Blair's minions.
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." Bart hangs a while on the edge. He goes to her house the next day, seeking comfort and solice. Chuck agrees to this, responding, "Let's get the bitch."
Chuck finds out that Dan releases the tape in Blair wedding causing Blair to blame him for releasing it. 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. While there, he says that he has no family and refuses to talk to anyone rationally. He then invites her to go and christen the penthouse.
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. Blair reluctantly goes back to Louis, despite an offer from Chuck to pay her dowry. She and Dan get a hotel room, where Chuck and Serena finally find them.
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Chuck Bass birthday