Jenny creates a fashion collection overnight and plans to take over a charity ball in order to get attention and hopefully attain funding. This plan temporarily turns awry when Dan finds her loading clothes out of the apartment and finds out that Jenny no longer works for Eleanor. He is worried about Jenny.
The Teacher's assistant from Yale has not gotten Dan letters of recommendation. Vanessa also has been avoiding the Humphrey place ever since Nate moved in.
The big shots over at Yale find Serena delightful and Serena tries to make Blair appear just as great by getting her a job as the babysitter of the dean's friend. She has a bad experience taking the 13-year old girl, Emma, to the movies. Meanwhile, Emma, is having a contest with a girl named Muffy as to who will lose their virginity first.
Chuck messes up Blair's plans to take Emma to the charity gala and instead they end up in a cab headed downtown.
Blair and Chuck come up with a scheme to save Emma from wanting to have sex. They generate a Gossip Girl post about how Muffy's "muff" had been "stuffed." Blair tells Emma that a girl's first time should be with someone special. After Blair's speech to Emma about talking to her mother instead of getting her attention by acting out, Emma tells the dean that out of everyone, she would most like to have dinner with Blair. This is a good sign for Blair and her Yale aspirations.
Serena tries to catch up with Aaron, but every time she does, there are other girl s around him.
Jenny's guerilla fashion show turns out to be a success. Everyone seems to be really enjoying themselves. All of a sudden, Nate kisses Jenny. Vanessa sees this and leaves. Jenny goes after her rather than staying with Nate. This makes Nate want to get out of the Humphrey home and move in with his mom. Before he leaves, he drops an envelope in the mail addressed to Jenny.
After, Rufus turns Jenny into the cops for how she handled the whole fashion show situation. Jenny decides to gather her stuff and run away.