Jenny (Taylor Momsen) comes home with mom Alison and asks them to talk and make up. Rufus (Matthew Settle) makes passive-aggressive comments toward Alison about how loyal he is. Dan comes home from his breakfast date to find the Humphreys at the breakfast table. He's not happy.
Serena and Dan are making out at a cafe, when Vanessa, who is now working there, interrupts them. Serena tells Blair about the awkwardness with Vanessa. Blair covers up the fact that she broke up with Nate.
Speaking of which, Nate's mother bailed his father out of jail to the tune of $1 million. Mom asks Nate to give Blair the Archibald family engagement ring as a birthday gift in order to appease Eleanor Waldorf, who is pissed about Mr. Archibald's arrest and wants out of their business deal.
The pressure is too much for Nate to handle, so he goes over to Chuck's to talk. He confides that his mom pressured him to give Blair an engagement ring so that the Waldorfs don't back out of their business deal. Chuck advises him not to cave to his parents. Yet Chuck has his motives - a diamond necklace Blair "reserved" at her favorite luxury jewelry store has been purchased (which she knows), but not by Nate. Hmm,
Alison tries to talk to Dan, but he's resentful toward her. He leaves and spends the day hanging out with Vanessa, who invites herself to Blair's birthday party with him when he says she should get to know Serena (Blake Lively) before being a brat towards her. This should go really well.
At the party, Blair is not happy when Chuck shows up, and even more thrown off when he admits - as only he can - that he has feelings for her. Chuck makes a wager with her that Nate won't show up or call her.
Nate finally arrives, but finds Jenny outside. They get to talking and go for a walk, both of them too nervous or upset to actually go inside. Dan and Vanessa go in, though, and after initial awkwardness, Serena tries to make an effort to bond with Vanessa, and asks her to play Guitar Hero.
Things are going well but Vanessa lets slip that Dan's mom is back, which upsets Serena - not just for Dan's sake, but she's hurt that Vanessa knew before she did. She walks away but Dan (Penn Badgley) promises to make it up to Serena and that she won't be second fiddle in his life.
Nate and Jenny are sitting on a stoop, having a great talk about life and relationships. Midnight passes and he doesn't call Blair. Nate hails a cab for Jenny and as they hug goodnight, one of Gossip Girl's underlings gets a pic of them on a camera phone and sends it to Blair. OMG! Jenny's face is not visible in the photo, but Blair is devastated when she receives the photo via text from GG.
Alison tells Rufus that her life has been about him, even when he was on the road on tour for months, and now she needs him to try to make it work with her. Nate also goes home to his parents and tosses the ring aside, saying he's not going to cave - and for his dad's sake, prosecutors had better not put him on the stand.
Blair breaks down at the party and tells everyone that she and Nate broke up, storming off to be alone. But Chuck (Ed Westwick) swoops in with the diamond necklace that he bought for her. He puts it seductively around her neck, offers his sincere sympathies for her breakup, and makes his move. Serena goes to comfort Blair, only to find them making out...
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