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It's Chuck and Jack doing battle again, only this time Elizabeth makes it possible for Jack to pull off a grand scheme and take the hotel.
Two security guards come up to Chuck’s room to tell him he must vacate the premises. When Chuck tries to set them straight, the guards tell him that the orders actually came from her.
Jack explains to Chuck that he’s been played.Elizabeth looks like she is sorry, but she doesn’t do anything to remedy the situation.
Jack takes over Chuck’s room. Chuck hopes that he can convince his mother to change her mind and give him back the hotel. He meets with her one-on-one and practically begs her to sign the hotel back to him and forget Jack.
But Elizabeth explains that she can’t do that because she loves Jack. Yes, she says that she is in LOVE with Jack. Chuck tries to tell her that she’s going to get hurt and that Jack is incapable of loving anything.
It turns out that Chuck was right and Elizabeth winds up getting her heart broken by Jack Bass. In an effort to help her son, Elizabeth give Jack an ultimatum and says that he needs to take her or the hotel.
Unsurprisingly, Jack chooses the hotel.
Elizabeth meets with Chuck and explains what happened. She says she signed the hotel over to Jack and that she is leaving town. He asks her to stay, not for Jack, but for him, since she is his mother.
But Elizabeth tells Chuck that she is not his mother and that she has to leave. Chuck seems to believe her because he can’t imagine that his mom would have put him through this, and they both go their separate ways.
But Elizabeth really is Chuck’s mother. That doesn’t stop her from leaving, as she tells Jack that she is going to start over, but we know.
Chuck ends the episode in the arms of Blair, vowing to get his revenge on Jack and get his hotel back. Will he get it?
Jenny gets back into the fashion game, working once again for Eleanor Waldorf.
At first, Jenny isn’t too thrilled about the idea, but once she gets into working again, she realizes how much she missed fashion.
Eleanor explains that she believes in second chances and holds nothing against Jenny for how everything ended between them.
And Eleanor surprises Jenny by saying that she hired Agnes back.
Agnes is supposedly sober, going to AA meetings and they become friends again. Jenny tells Agnes about how Damien won’t leave her be and wants his pills back, Agnes comes up with a plan to get back at him.
Agnes suggests they invite Damien to the fashion show to set up the exchange for the pills and then flush them down the toilet while he is there.
Agnes figures that will teach Damien a lesson.
But Eleanor praises Jenny and says something about making her position permanent with Waldorf Designs, so Jenny decides not to go through with the whole Damien scheme.
She tells Agnes that she doesn’t want to mess anything up with Eleanor this time around. Agnes pretends to understand, but she ends up stealing all the pills from Jenny’s purse.
Agnes is still bitter and jealous of Jenny. At the fashion show, Agnes gives all the models some of the pills and then slips three into a congratulatory drink for J at the end.
By the end, Jenny can’t see straight or stand up on her own.
Agnes pushes Jenny into a cab and drops her off with some unknown men at a bar. Just as one of the guys is about to take advantage of drugged Jenny, Nate comes to her rescue and takes her home.
Nate gives her a pep talk about how things will change for her and how things will turn around. Right after that, Jenny gets a phone call from Eleanor offering her a job.
So things are starting to look up a bit for Jenny, but I wonder how long that will last. Jenny likes to play games and cause trouble, so I’m going to guess that she won’t play the good girl for very long.
Vanessa and Dan have taken their relationship public. Well, actually, Serena and Nate took Vanessa and Dan’s relationship public.
They end up telling Rufus the news so everyone is already aware that Dan and Vanessa are dating when they show up at Rufus’ for breakfast.
Although everyone seems happy about the fact that they are dating, Vanessa begins to think that her and Dan are in a rut because they do the same things they did as friends.
And after hearing that Nate and Serena constantly change things up to keep their relationship fresh, Vanessa decides that she wants to do something special to surprise Dan.
Serena and Nate suggest role-playing and Vanessa decides to recreate a scene from one of Dan’s favorite films. So she dresses up and sets a dinner scene from “Rear Window.”
Dan appreciates what Vanessa did, but he seems like he would rather have just done what they had planned (hang out).
Vanessa gets upset because Dan just wants to do the same things they did as friends and she walks out on the date.
Later, Dan goes to visit Vanessa in her dorm room and explains that he will give her the most romantic second first date that she’s ever had.
That includes ordering pierogies to the dorm room and hanging out.
When Vanessa seems unconvinced about the romance, Dan explains that he’s just happy being able to do the same things with Vanessa, but this time, couple style.
Blair bribes prostitutes to come to her mother’s fashion show and pretend to be her friends (because Blair has no friends at NYU) and classic, All-American girls to help Eleanor score a big retail client.
Cromwell recognizes the working women in the crowd, however.
When Blair confronts Brandice, she explains that Cromwell knows Julian, a gay prostitute that she invited to attend the show.
Blair has a way to blackmail Cromwell and she uses it to her full advantage.
She gets him to agree to carry Eleanor’s line in his stores. However, when he gives Eleanor the news, he also suggests several changes to the line, including a name change.
Eventually Eleanor refuses the deal and tells Blair that she doesn’t want to lose who she is. She also tells Blair to stay true to herself.
This makes Blair finally confess to her mother that she doesn’t have any friends at NYU and doesn’t fit in. Blair doesn’t belong at NYU.
But, at the end, she is approached by girls from Columbia who know who she is and fawn over her.