In Season 5, Episode 15 of Gossip Girl (aka “Crazy, Cupid Love,”) the Upper East Side is celebrating Valentine’s Day.
- Blair is Back – Apparently Louis didn’t trap her in a castle as we had originally thought. She’s back in town expect she now has a royal escort named Estee who is basically spying on her to make sure she doesn’t go back with Chuck.
- Nate Gets Dissed by Lola – Short of needing a restraining order, Nate bribes Lola’s boss and gets her phone number to ask her out. She blames having to work and then basically disses Nate to his face (but in her defense, he was being creepy!) Georgina/Gossip Girl manipulates Nate into throwing a party at The Spectator and he’s excited because he can ask for Lola to be the waiter. But, when he calls to ask for her, he finds out that she has a note in her file saying she’s not to work any Spectator parties. Confirmed diss!
- Blair and Dorota Play Cupid – Dan and Serena both separately mention to Blair that the best V-Day they’ve had was with each other. So, B wants to get the two of them together and arranges both of their lunch dates to stand them up so they end up having champagne and dessert on the house (er, Blair) together at the restaurant.
- The Throwback Party Happens at The Empire – Chuck helps out his boy Nate and calls to get Lola to cater the party at The Empire. Everyone is supposed to dress up like their high school selves. Lots of Constance Billard uniforms happening (and Nate looks so sexy!) Georgina/Gossip Girl texts Dan and tells him that he has to bring Blair or else she’ll release a video of Blair. He says he wants her to go and help him and Serena get back together. But at the party, Georgina/Gossip Girl texts Dan and tells him to kiss Blair. He finds out that Georgina is the one texting him. But then! He kisses B anyway and the door opens. Georgina snaps a pic and Serena is also standing right there. Oops!
- Ivy/Charlie is Back – She’s come looking for Lily and when she can’t find her at the Humphreys’ house, she heads to Nate’s party and comes face-to-face with Lola… who she knows! The girls were in an acting class together back in Florida. They reminisce and then Ivy heads out. But Nate drops the bomb on Lola that Ivy is basically stealing her identity with the way he’s talking about her. Creepy!
- Chuck Hooks Up with Alessandra – After Georgina shows Chuck the pic of Dan kissing Blair, Chuck takes Dan’s book agent Alessandra (who was basically throwing herself on him earlier that night) back to his place. We can only assume she’ll be used in the war against Humphrey that’s about to happen.
- Something’s Wrong with CeCe – Ivy/Charlie goes to this fancy house and a nurse walks in talking about the woman in the other room. Then the camera pans on a photo of Ivy with CeCe.
What did you think about this episode? Leave your thoughts in a comment below!









