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It's the night of the masquerade ball - and Blair has a scavenger hunt in mind for Nate. The prize if he gets through it? Her. If you know what we mean!
Meanwhile, Dan receives a shock when his former girlfriend, Vanessa, shows up at this apartment. She's now back in the city, living in with her sister after spending time the last year in Vanessa with her mom. This is confusing news for Dan, as Serena calls to invite him to the ball... only to overhear Vanessa in the background and see right through Dan's lie that it's his sister (because, at that moment, Jenny shows up there Serena is on the phone, Blair's apartment). Serena never invites Dan and quickly hangs up, distraught.
At this, Blair gets every single guy she can find to ask Serena to the party. She accepts one of their invitations, over Instant Messenger, of course.
During this time, Jenny is running around as Blair's slave. So much for standing up to her last week. But despite her efforts, Jenny does not snag an invite to the ball. Also, Nate finds a stash of drugs inside a book at his house and assumes it's his father's. And just what is the elder Archibald up to?
He and the Mrs. are at a shindig thrown by Eleanor Waldorf, as Mr. Archibald is trying to land her business. At this same party are Rufus and Lily because she invited him to make Bart Bass jealous. But is there an actual spark between Rufus and Lily? It seems that way when he kisses her... to help make Bart jealous, naturally.
Now, back to the younger set: Dan decides to go to the ball and surprise Serena, canceling a date with Vanessa in the process. She then meets up with Jenny in the Humphrey apartment and helps her sneak into the ball. Once inside, Jenny is hit on by an old nemesis: Chuck, who apparently can't recognize Jen through her simple little mask. She is obviously seeking revenge, telling Chuck to leave a trail of clothing for her to follow.
We'll get back to that shortly, but first Dan and Serena sort out their differences inside the party. Dan explains who Vanessa is and that he's only interested in Serena now. They kiss passionately... only for Vanessa to witness because she was trying to find Jenny and give her back her apartment keys). Awkwardness ensues. And Vanessa throws out a bombshell when Dan catches up to her: "You said you loved me."
But at least Dan is honest now, he admits that he loveD her. Now, a lot has changed. Still, when Vanessa runs out, Dan tries to catch up with her. Serena is left very confused.
Until she runs into Jenny in the bathroom (who, of course, locked Chuck on the roof in his underwear). Jenny explains that Dan seriously does care about her... but also that she has to leave before midnight, lest she incur Chuck's wrath when the masks come off. In a move that will get them both in trouble, Serena and Jenny switch masks, while Serena also gives little Humphrey her shawl. Time for cases of mistaken identity:
Nate reveals he still has feelings for Serena, only he doesn't know he's talking to Jenny. After Jenny runs away, though, Serena grabs Nate and says he has to go find Blair. Dude is confused, but does as he'd told. Meanwhile, Blair tries to stop who she thinks is Serena - to ask where Nate is - only for Jenny to blow by her, leaving only her bracelet behind. Blair recognizes it and knows Jenny attended the ball against her orders.
And now Chuck knows this, as well. Little J is making some enemies.
Near the end of the episode, Nate arrives home to find his parents trying to celebrate the fact that his father has landed Eleanor Waldorf's account. But there's a problem: they've also found the drugs. And Nate's father silently tells his son to take the blame. Nate abides.
We end the hour with Dan and Serena kissing yet again. He says he likes her and only her and that Vanessa is in the past. However, when he returns home, Vanessa is there. But she comes in peace. She says it's okay, they can go back to being friends. And the credits roll with Dan telling her all about Serena.