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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 "stays 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 alone 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 make up and find an another game to play, which involves only the two of them and some role playing.
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 demonstrate 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 humiliated. When Blair shows up at the premiere to let Jenny have it, Chuck confesses that 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".
In episode "Enough About Eve", Blair's plan (with is to get to toast at the Freshmen Dinner at Parent's Weekend) involves reinstituting her and Chuck's game from the summer… with a little twist. Blair tells Chuck that she needs him to seduce Josh Ellis so she can humiliate him, as he double-crossed her, and Chuck goes along with it. Blair interrupts the scene right after the big kiss, and pretends to make a big scene. Though really she made a deal with him, she gets to make the toast, and he gets to kiss Chuck Bass. Chuck's plans get cancelled so he shows up at the dinner and gets a little too much info from one of Blair's new minions. Then he sees Blair and the man he kissed talking and laughing and he realizes something is definitely up. Blair's speech was about breeding and wealth, etc. and she even mentions that she had to trick Chuck into getting it (though Blair doesn't known Chuck's there). Blair goes over to Chuck's to apologize and it is clear he needs some more time to think about it.
In the next episode Chuck and Blair are talking again, though he is short with her. Chuck is trying to find a way to boost his hotel's ratings and decided to open the club. He calls Serena for help, but instructs her to leave Blair out of it (not knowing that Blair is listening to the conversation). Blair calls Jack Bass and gets him to send over a liquor license for Chuck, desperate to help out. Later Chuck comes to Blair's and gives her a costume for the club's opening, and they briefly make up. This is ruined when Chuck finds out she called Jack. Chuck tells her that he kept her out of opening the club for the same reason it took him so long to tell her he loves her; he can't trust her. He uninvites her to the opening but Blair shows up anyway after finding out the liquor license Jack sent over was a fake. Blair apologizes to Chuck and tells him that she was trying to make him see that he needed her. Chuck tells Blair that he already knew the license was a fake, and the two quickly come up with an idea. Chuck calls the police and has them shut down the club, while Blair makes sure the paparazzi gets pictures of the celebrities present. Chuck decides to open a secret club, and by the end of the episode Chuck and Blair have made up.
In the episode "The Debarted", On the anniversary of Bart Bass' death, Chuck wrestles with the dilemma of following his conscience, or that of his father. While visiting his father's grave he see's Mystery Woman lying yellow flower's on his gave.
In the episode "The Lady Vanished", Chuck learns that Mystery's Woman's name is Elizabeth Fisher and she may be his mother.
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.
In the episode "Inglorious Bassterds", Jack says he will give back the hotel to Chuck but only if he gets to spend the night with Blair. Thinking Chuck doesn't know about it, Blair agrees to spend the night with him but only if Chuck will never know. Jack kisses Blair, then tells her that Chuck did know and did this to trick her. The two breakup and Chuck gets his hotel back.
In the episode "The Unblairable Lightness Of Being", Chuck is desperately trying to get Blair back and apologizes to her. While Blair really wants for them to get back together, she refuses because of the disgust she feels for still loving him even after the way he acted. Blair feels it is not right to go as far as she did to help a person, no matter how much you love them; considering what she did for Chuck, she couldn't live with herself if she stayed with him. Chuck begged Blair to stay with him, and to not end their relationship, but Blair ultimately said it was the end, causing him to go back to seducing any woman he desired, only to get over how devastated he is.
In the upcoming episode "Dr. Estrangeloved", Chuck will go to great lengths to get either his girlfriend Blair or his best friend Nate back in his possession. In order to do this, Chuck enlists the help of Jenny, who has been after Nate ever since her breakup with Damien, to break up Serena and Nate. Chuck decides to try and end their relationship because he believes it will make it easier for him to get back the people he lov
es.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 demonstrate 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 humiliated. When Blair shows up at the premiere to let Jenny have it, Chuck confesses that 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".
In episode "Enough About Eve", Blair's plan (with is to get to toast at the Freshmen Dinner at Parent's Weekend) involves reinstituting her and Chuck's game from the summer… with a little twist. Blair tells Chuck that she needs him to seduce Josh Ellis so she can humiliate him, as he double-crossed her, and Chuck goes along with it. Blair interrupts the scene right after the big kiss, and pretends to make a big scene. Though really she made a deal with him, she gets to make the toast, and he gets to kiss Chuck Bass. Chuck's plans get cancelled so he shows up at the dinner and gets a little too much info from one of Blair's new minions. Then he sees Blair and the man he kissed talking and laughing and he realizes something is definitely up. Blair's speech was about breeding and wealth, etc. and she even mentions that she had to trick Chuck into getting it (though Blair doesn't known Chuck's there). Blair goes over to Chuck's to apologize and it is clear he needs some more time to think about it.
In the next episode Chuck and Blair are talking again, though he is short with her. Chuck is trying to find a way to boost his hotel's ratings and decided to open the club. He calls Serena for help, but instructs her to leave Blair out of it (not knowing that Blair is listening to the conversation). Blair calls Jack Bass and gets him to send over a liquor license for Chuck, desperate to help out. Later Chuck comes to Blair's and gives her a costume for the club's opening, and they briefly make up. This is ruined when Chuck finds out she called Jack. Chuck tells her that he kept her out of opening the club for the same reason it took him so long to tell her he loves her; he can't trust her. He uninvites her to the opening but Blair shows up anyway after finding out the liquor license Jack sent over was a fake. Blair apologizes to Chuck and tells him that she was trying to make him see that he needed her. Chuck tells Blair that he already knew the license was a fake, and the two quickly come up with an idea. Chuck calls the police and has them shut down the club, while Blair makes sure the paparazzi gets pictures of the celebrities present. Chuck decides to open a secret club, and by the end of the episode Chuck and Blair have made up.
In the episode "The Debarted", On the anniversary of Bart Bass' death, Chuck wrestles with the dilemma of following his conscience, or that of his father. While visiting his father's grave he see's Mystery Woman lying yellow flower's on his gave.
In the episode "The Lady Vanished", Chuck learns that Mystery's Woman's name is Elizabeth Fisher and she may be his mother.
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.
In the episode "Inglorious Bassterds", Jack says he will give back the hotel to Chuck but only if he gets to spend the night with Blair. Thinking Chuck doesn't know about it, Blair agrees to spend the night with him but only if Chuck will never know. Jack kisses Blair, then tells her that Chuck did know and did this to trick her. The two breakup and Chuck gets his hotel back.
In the episode "The Unblairable Lightness Of Being", Chuck is desperately trying to get Blair back and apologizes to her. While Blair really wants for them to get back together, she refuses because of the disgust she feels for still loving him even after the way he acted. Blair feels it is not right to go as far as she did to help a person, no matter how much you love them; considering what she did for Chuck, she couldn't live with herself if she stayed with him. Chuck begged Blair to stay with him, and to not end their relationship, but Blair ultimately said it was the end, causing him to go back to seducing any woman he desired, only to get over how devastated he is.
In the upcoming episode "Dr. Estrangeloved", Chuck will go to great lengths to get either his girlfriend Blair or his best friend Nate back in his possession. In order to do this, Chuck enlists the help of Jenny, who has been after Nate ever since her breakup with Damien, to break up Serena and Nate. Chuck decides to try and end their relationship because he believes it will make it easier for him to get back the people he lov
