- Blair comes up with a plan to get revenge on her teacher; Chuck wakes up in a hotel and tries to piece together what happened the night before.
- The twisted Blair plans a cruel revenge against her teacher, Rachel Carr, for her one bad grade, but has problems getting her posse of mean girls to rally for support since they are not keen to taking on a teacher. So, Blair starts a rumor that Miss Carr and Dan are romantically involved, which creates a firestorm of gossip, and she has her father, Harold, to back her up. But the final blows comes when Serena sees Dan and Rachel meeting at a local coffee shop and jumps to the wrong conclusion which Blair sees off her greatest victory, but also her most bittersweet one. Meanwhile, Chuck calls upon Nate and Vanessa for help when he wakes up in a strange hotel room and seek out a mysterious woman he met at a mysterious secret society party the night before which may had drastic consequences for him.—matt-282
- After hearing the news about Blair mistreating the newest Constance teacher, Rachel, the headmistress decides to punish Blair with a detention, jeopardizing her acceptance at Yale.
Blair completes her punitive duties (or rather, makes Deroda complete them), and gets back into the good graces of the headmistress, securing her spot at Yale once more. However, Blair is still hell-bent on revenge. Showing resistance to her incessant demands, Blair's followers think she should brush it off, since she no longer has to worry about Yale.
After the school decides to ban cell phones, Blair's minions have a change of heart since they suspect Rachel is behind the prohibition. They are desperate to dig up any scandals about Rachel's past, but to Blair's disappointment, it seems that there's no dirt on the new teacher...until Blair happens to see a flirtatious exchange between Rachel and Dan in the hallway.
Meanwhile, Serena and Dan are having problems dealing with the fact that they are headed to different universities. Serena also begins to notice a strange connection between Dan and Rachel and, to her surprise, bumps into them having coffee together.
Lacking any concrete proof, Blair decides to create a false rumor that Dan and Rachel are having a relationship. This makes Serena uneasy, even though Dan tells her the story is ridiculous.
News of the rumor and the Gossip Girl phenomenon gets to Rachel via Serena. Upset and outraged, Rachel tells the headmistress who then organizes a parent/teacher meeting regarding the removal of the gossip website. Dan finds out that Blair is behind the rumor and proceeds to notify the headmistress in order to protect the reputation of himself, but moreover, Rachel. Fed up with Blair's shenanigans, the headmistress expels Blair, destroying her hopes of Yale. Unable to do anything else, Blair reluctantly admits defeat. Blair's father tries to comfort his daughter and tells her that they will fight the expulsion since he believes Blair is telling the truth about the affair.
Serena is upset about Blair's expulsion, and talks to Rachel in hopes of reconsidering the punishment. Rachel stands firm. When Rachel accidentally leaves her notebook behind, Serena can't help but leaf through it, noticing a scheduled meeting at a cafe later that evening. Serena decides to head to the address, but when she looks through the window, she sees Dan and Rachel having coffee over candlelight. Rachel is crying and Dan gently brushes her hair to console her. Serena, thinking the worst, snaps a picture of the pair with her cell phone and rushes off to Blair's apartment. Dan further tries to console Rachel, but Rachel's common sense makes her back away, telling Dan it's completely inappropriate to have any contact. Dan apologizes, and Rachel jokingly tells him that if things were different--if Dan were older and not her student--maybe things could be different. Serena tells Blair about the picture, which Blair sees as her chance to prove she was telling the truth and not committing slander. The picture goes up onto Gossip Girl.
Serena calls Dan and arranges to meet him at the school to confront him. Blair crashes the parent/teacher meeting at Constance and reveals the scandalous photo to the surprised onlookers, including Rachel. Once Dan and Serena meet at the school, Dan assures her that it is all a misunderstanding. Serena believes him, and tells Dan that Blair has the picture and is inside the parent/teacher committee. At that moment, a classroom door opens, and Rachel exits tearfully saying she's just been fired. Blair boasts about her victory to Serena and Dan, but doesn't realize that her father is listening behind her. Disappointed about Blair's lack of morality and lies, Blair's father leaves the school.
Dan and Serena have a discussion about their relationship and decide that it's over. It seems there are too many problems that come between them. They will part amicably.
The next day, Serena tries to apologize to Rachel for her part in spreading the rumor, but Rachel asks her to leave.
That night, Dan also goes to Rachel's apartment to apologize for acting inappropriately at the cafe. To his surprise, Rachel kisses him. To the audience's surprise, Dan kisses Rachel back! Rachel says she's no longer a teacher at Constance, and pulls Dan into the apartment.
The headmistress has a talk with Lily and Rufus about the scandal and says that the school cannot be in the public spotlight for this type of thing. She also says that she is convinced Dan is telling the truth and that the school can't risk a lawsuit from Rachel. The school will drop the case and allow Rachel to return as a teacher. Serena tries to call Dan to say she wants to forget their earlier conversation about breaking up...it sounds like she wants to give it another chance. The headmistress tries to call Rachel to apologize and rehire her. Dan and Rachel's cell phones ring on the bed while they're making out.
Side Story: Chuck wakes up in a hotel with little memory of what happened the previous evening. He has what looks like a tattoo on his wrist and an anonymous invitation to an address. The only image in his mind is of a beautiful, masked seductress and he is desperate to track her down. Chuck invites Nate and Vanessa to join him as he retraces his steps. The invitation leads them to a luxurious, but empty apartment that's up for sale. Chuck sees a picture of a woman holding a baby, and is convinced that this is his dream girl. He eventually finds her (Elle) and discovers that she is a nanny, moonlighting as a high priced call girl who services wealthy and powerful men belonging to a secret society. Bart, Chuck's father, was supposed to be her client, but Chuck received the invitation accidentally. The girl asks that Chuck never contact her again and to forget about the secret society. Chuck goes home and rifles through his father's safe to find a stack of invitations in a black box.
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