Jenny is frantically sewing away to get ready a "guerrilla" fashion show - which will crash the New York Philanthropist Society’s annual gala.
Serena and Blair are putting on a little show of their own in the home of a female Yale donor and a close friend of the Dean.
The purpose of their visit seems to be to get Blair in good favor so that she can get into her dream college. However, the woman seems to only be interested in Serena and her celebrity status.
As the two pals are about to leave, Serena tells the woman that Blair would be happy to take her daughter out to a movie, hoping this will finally get Blair through the door.
As Serena leaves the building, Aaron meets up with her in the courtyard and asks her if she figured out the caterpillar story. She tells him she did, but just as she is about to invite him to the gala, a brunette runs up to kiss Aaron on the cheek and Serena awkwardly leaves.
Blair’s project, Emma, seems to be a bit more than Blair can handle.
As soon as her mother leaves, the young teen says that she wants to lose her virginity before her friend Muffy (so classic) does and she is planning to do it on Blair’s watch.
Serena suggests that they take her to the gala event that evening and tell her that there will be a ton of elite guys she can choose from - when in reality it'll just be older people.
Emma gets dressed up in one of Serena’s dresses, but as Blair and Serena are getting ready, Chuck introduces himself to her. She knows who Chuck Bass is and wants to give up her v-card in the back of his limo.
Chuck doesn't bite.
He tells Blair of Emma's intentions, and Blair starts to rail on Chuck about how he has a thing for virgins and he tells her that the backseat of his limo is something he holds sacred.
The three of them go to find Emma who has now escaped.
Jenny and Agnes are just about to walk out the door with all their dresses in tow when Dan and Nate walk in and find them. The two guys were supposed to be at a movie, but a text-message sent to Dan’s phone from Jordan (the Yale girl) about his stories cut that short.
Jenny explains to Dan what she is doing and promises that she will tell her father about it the next day. Dan goes into big-brother mode and doesn’t give her his approval. Instead he goes to visit Vanessa.
Vanessa supports Jenny’s idea and is sticking up for her. Then the topic of conversation turns to Nate and Dan sticks up for him despite the fact that Vanessa says he’s done some pretty bad things.
Jenny decides that she can’t wait on Dan’s decision, despite the fact that Nate is trying to convince her to think about what she's doing a little bit more and hold off until Dan comes back.
Jenny gets upset with him and yells at him for not talking to her for the past week. Nate explains there are a lot of complications but he agrees to go along to the event because Jenny says that it will mean a lot to her.
Rufus and Dan see the van just as it is driving away and both of them start to get extremely concerned about Little J.
Jenny failed to tell Dan where the event was taking place, so he has no idea where she if off to and Rufus, him and Vanessa frantically start to call her and try to figure it out.
While Blair and Chuck are desperately searching for Emma, Serena is swooning over the licorice ring that Aaron sent to her apartment earlier in the day.
The crew eventually spots Emma in a bar, getting friendly with a guy named Serg. Just when they are about to collect Emma, Serena gets distracted by some guy that she knows which gives Emma a chance to bolt again.
But that turns out to be a blessing in disguise. As they try to hunt her down, Chuck points out Emma’s mom making out with a man in the corner.
Blair snaps a picture.
At the gala, which Lily and Bart are being honored at of course, Jenny manages to get past security by saying that she is Erica van der Woodsen.
However once she is inside Jenny gets extremely nervous about the show and the implications that it might have on Lily and Bart — two people who have been extremely nice to her in the past.
Nate shows up in the tuxedo that Jenny rented for him (amazing that it fits so perfectly) and rescues her from Lily’s questioning.
Nate says that his mother couldn’t make it so he came in her place and decided to bring Jenny along.
Nate shows his support for the young fashion designer by kissing her. Hard.
Someone sees it and sends a photo to Gossip Girl.
Dan happens to be checking Gossip Girl and sees the picture.
Dan tells Rufus and Vanessa where they can find Jenny and the three of them hop in a cab in order to get there.
Blair and Chuck decide to devise a plan in order to get Emma out of harm’s way, virginity still in tact. They get Gossip Girl to post false info about Emma’s friend losing her virginity.
The title is called “Muffy’s muff gets stuffed.” ROTFLOL.
Chuck and Blair show up at Serge’s apartment just as Emma is about to do the deed and show her the Gossip Girl site. She can’t believe that her friend lost her virginity first and decides to leave.
When Blair drops Emma off at her apartment, the teen goes storming towards the elevator. Blair catches up to her and offers her some advice about how a girl’s first time should be with someone they love.
When Emma asks if Blair’s first time was with someone she loved, Blair, all teary-eyed, says that it was. Awesome moment.
Blair talks about the problems she’s had with her own mother and explains to Emma that she should try talking to her mother instead of acting out.
Emma takes Blair’s advice and the two suddenly seem to be friends. Blair walks her back up to the apartment where Emma’s mother is waiting.
She gets angry and blames Blair for corrupting her daughter and tells her that she is “not Yale material.” Blair is about to pull out the photo she snapped in the club, but takes the high road instead and tells the woman that she really should spend more time with her daughter.
On her way to the gala, Serena phones Aaron and gets his voicemail.
He has recorded a message that is specifically directed to her and she can’t help but find it sweet. She begins to leave a message about wanting to give him another chance, but then the phone is picked up by a girl named Tamra, who asks if Serena is looking for Aaron. Serena hangs up.
At the gala, Dan, Vanessa and Rufus show up looking for Jenny and are met at the door by Lily, who lets them in and Bart seems really annoyed by the fact that Rufus is there. Dan goes to find Nate and when he does, screams at him for being with his 15-year old sister.
Nate tries to explain, but Dan calls him out on all the bad things he’s done in the past and kicks him out of the Humphrey abode. Dan also learns that none of the professors from Yale will write him a recommendation letter.
Jenny’s fashion show goes off without a hitch. The lights go off, a video plays in the background, music plays and the models storm the room.
Flyers and postcards are thrown all over the room advertising Little Jenny’s designs. Everyone seems impressed — that is, everyone except for Vanessa who sees Jenny run into Nate’s arms after the show.
She storms out and Jenny runs after her.
Outside, Rufus is furious about how Jenny handled the situation and even turns her over the cops. But before the cops can take her down to the station, Lily intervenes and says she will not be pressing charges.
When Rufus tells Lily that it is none of her business, Lily explains that she doesn’t want Rufus to make a huge mistake.
In the morning, Rufus finds out that Jenny has taken most of her belongings and run away.
Inspired by how Jenny went all-out for what she wanted, Dan mails the manuscript to the Paris Review Editor - the story about Chuck Bass.
In the morning, Serena is comforting Blair about Yale when Blair gets a call from the Dean of Admissions at Yale who explains that Emma spoke kindly of her and that Blair would make a wonderful addition to the school.
While Blair is busy chatting up the Dean, Aaron shows up again and proposes to take Serena to breakfast. He thinks that fate has brought them back together and asks Serena out to dinner.
Serena agrees and seems giddy over him.
Nate leaves to live with his mom, but places an envelope in the mail addressed to Jenny before he goes.
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