The episode open with Blair dreaming that she is the lead in "Wait Until Dark," and someone is trying to kill her. It appears that Serena has hooked up with Colin, the guy who continuously stole her cab before class. Nate is headed to visit his dad in prison. Nate and Juliet finally slept together, but when Nate wake's up, Juliet left a note saying she was late for class. When he gets to the prison, Nate gets more than he bargained for when he runs into Juliet, also waiting to get in. It turns out that Colin is the new Psychology of Business Professor, and Serena is none to pleased. Blair has a sick feeling in her stomach that something is going on with Jenny, so she heads over to Rufus and Lily's she finds that Jenny is, in fact, home. Jenny managed to get and interview with Tim Gunn to get into Parson's, so she will only be there for the day. Blair reiterates that she banished Jenny last year for a reason, and Jenny needs to leave. Jenny manages to get a "day pass," so she can go to her interview; but she is not to go anywhere but to the interview and the train station. Nate and Juliet sit down to discuss why they were each at the prison, and Nate comes clean about his dad. Juliet lies, yet again, when she said that she was there to volunteer for the prison literacy program.
When Chuck finds out that Jenny is home, he stops by the loft to apologize for everything. Dan runs interference and tells Chuck that he needs to leave, which he does, but not before swiping Jenny's portfolio. Colin catches up with Serena after class, and we learn that nothing actually happened the night before. Serena tells him that she can't continue anything with him, because student/teacher relationships are forbidden. Regardless of Serena's concerns, Colin asks her out. He tells her that he is willing to give up his bachelor status, if she is willing to put off the class for one more semester. She agrees to the "deal," and they plan for the evening ahead. Chuck calls Jenny and tells her that he picked her portfolio up by mistake when he was getting some papers from Lily. When she tells him that he needs to bring it back , he says that he can't and that she is going to have to come to get it. Blair has her minions following Jenny's every move, so when she shows up at The Empire they call her to let her know. Blair calls to get the address of Tim Gunn's studio. She is out for blood.
Ben really is Juliet's brother, and when she tells him that she doesn't want to lie to Nate anymore he says its ok; in reality, he goes to find Nate's dad. When Jenny's models come out to show Tim the line, they have the letters W-H-O-R-E spread across their fronts. Tim is not impressed with this, and asks Jenny to leave. Chuck calls and offers Jenny a second chance at talking to Tim Gunn, and Dan convinces her to take the opportunity. Chuck tells Dan that he will leave tickets for the whole family. This is definitely shaping up to be a ploy against Blair.
At the party, Serena is trying to explain to Lilly about her choice to put the class off for a semester to be with Colin, when Colin comes over and tells Lilly for her by kissing her in front of Lilly. Tim Gunn decides to give Jenny another chance, and her also warns her to not let her designs out of her sights. He also lets it slip that Chuck was the one who set the whole thing up. Juliet is about to tell Nate the truth about her family, but she gets interrupted when Nate gets a phone call from the prison. His dad was jumped and is now in the infirmary. After Nate leaves, Juliet gets a text from Ben making sure that she got the message that he wanted to send across. She is not to come clean to Nate about anything. As Jenny is getting ready to leave the party, she discovers that nobody actually knows the reason for her "banishment" from the Upper East Side, and decides its time for everyone to know the truth. Blair arrives at the party, and finally realizes that Chuck was behind all of it. He was the reason that Jenny was back, and he was also responsible for Blair knowing that Jenny showed up at The Empire. It was all a setup for Blair and it worked. Jenny sent a blast to Gossip Girl explaining everything. She was banished because she lost her virginity to Chuck. Dan tells Jenny that she should go back to Hudson if she is back to her old self after just one day back.
Lily decides to use reverse psychology on Serena to get her to fully realize her potential. As Jenny is leaving the party, she confronts Chuck and Blair and tells them that she is better than the games they play. She tells them that they are eventually going to destroy each other if they keep up with this war, and she makes it clear that she won't be returning anytime soon. The only chance of her even thinking of coming home would be if the war between them was finally over. Later that night, Chuck comes to Blair asking for a truce. The two shake hands and make it official, and it is more apparent than ever that they still love each other.
Colin and Serena agree to keep things professional until the end of the semester, so that Serena can take the class and hopefully "find" herself. Colin tells her that he can wait if she can. Juliet calls to talk to Nate, but Nate assumes that he is calling to break up with him because of his dad. She tries to tell him otherwise, but he doesn't want to hear it. He breaks it off. Juliet is sitting on the couch, when all of a sudden Colin walks in. It seems that Colin is the financial backer of whatever is going on with Ben and Juliet and there vendetta against Serena.
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