Dan Humphrey and Serena van der Woodsen haven’t seen each other since their breakup, so things are awkward. They try to be all grown up about it and skip to the friends part, but a new girl gets in the way. Amanda is her name.
She reads all of the same stuff Dan reads, so he immediately invites her to lunch, which was innocent enough but instantly triggers some class warfare.
Serena feels hurt, embarrassed and jealous. Blair Waldorf sees this and goes on the attack. She tries to befriend Amanda in order to bond her to the “girl code” and render her unable to date a friend’s ex. Chuck explains this to Dan, who is typically confused.
Amanda decides to rebel, though, and invites Dan to a club. Of course, this ends up on Gossip Girl, which pisses Serena off royally. However, she does not want things to be like this with Dan so she suggests the next night that all three of them - Amanda, Serena and Dan - go to the club on a "date."
It goes okay until Serena gets drunk and starts falling all over a Dalton lacrosse player. Blair’s creepy minions are there watching, as is Chuck.
Chuck’s entire purpose there is pure evil.
He's got some sort of Nair/bleach mixture in his pocket, which he provides Blair's minions with. Soon enough, they pour it in a cocktail glass and throw it into Amanda's hair, burning chunks of it off. That was cold.
Lily is back from her honeymoon and seemingly lonely, filled with regret. Bart is in Beijing on business, and Lily's back in New York. She doesn't come out and say it, but she is all of a sudden very interested in Rufus again. He sort of gives her the cold shoulder, though, reminding her that she made the decision to be Mrs. Bart Bass and now has to live with it.
Meanwhile, Nate is trying to figure out why the hell Vanessa spurned him like that. The Duchess is pleased with her "deal" with Vanessa and takes $5,000 to her to show her appreciation. Catherine leaves a check in the gallery / cafe and departs.
Vanessa, of course, decides to return the bribe in person and goes straight to Catharine’s apartment to do so. That's when she conveniently walks in on her and Marcus getting. It. On. Wow.
Turning to Dan, Vanessa wants to get Nate's (and Nate's dad) off the hook if she can but doesn't know how. V shows him the camera phone pic she snapped. Dan has no better advice than to tell her to seek out Blair, because she’s pretty much the empress of revenge.
Vanessa shares the info with a surprisingly distraught Blair, who is really sad about this actually, but nevertheless sets a plan in motion.
And plan she did! Blair confronts the Duchess and her man and negotiates a deal with Catharine and Marcus in which they leave town and pay off all of Nate’s father’s restitution in return for her silence.
But here's the twist. Not knowing enough to stay out of Blair’s way and let things take their course, Vanessa gets antsy and tells Catharine’s husband personally about everything. That infuriates the Duchess, and the deal is off. As far as the money goes, anyway. At least Nate is no longer a hooker and we've seen the last of Catherine.
With Blair preoccupied by Marcus and the Duchess, Chuck has been playing everyone so that Serena will reoccupy her queen status.
This includes hiring Amanda to pretend to have a crush on Dan to manipulate Serena to the top of the high school hierarchy and knocking Blair off her throne, then paying Amanda to transfer schools at the end of the charade.
He had to "create a monster" and it looks like he's done that in the new Serena (which he says is the old, real Serena).
(Source: TV Fanatic)