Happy Valentine’s Day! What is Valentine’s without love, budding romance, and disappointment?
Gossip Girl AKA Georgina is ready to reveal a whopping secret that would send people crying. The only problem is that she can’t quite get the scoop that she wants because it’s harder without those Upper East Side elites being in the same place at the same time. How does this get remedied? A “dress as you were in high school” party posted by GG and hosted by Nate. What better way to scoop up some drama then to go back in time.
Blair is back from her “honeymoon” with Louis and has come with company. No, it is not Prince Louis but her “royal minder.”
Her “social secretary” is there to monitor everything Blair does and everywhere Blair goes. Blair feels that since she cannot be in a love-filled marriage that she would help the people she loves most, fall back in love with each other. Blair makes this elaborate scheme to get Dan and Serena to try to rekindle their love. Of course, this would never work because Dan is madly in love with the matchmaker, Blair.
Nate is having a hard time trying to get his date for Valentine’s Day. Lola dismisses his proposal for a Valentine’s date and when Nate decides to host his high school party, he decides to get Lola and the catering company she works for to work the party. However, Lola has put in a request never to work a Spectator party. Of course it is sullen Chuck to the rescue as he decides to host the party in his apartment at the Empire.
Serena is upset by Blair’s gesture and wants to let the whole Dan thing go. Blair decides she cannot go to party at Chuck’s apartment and asks Serena to go to a fundraiser event instead. Dan also decides he does not want to relive his high school days and opts out of the party. This is until GG starts sending him text messages. GG wants Dan to make Blair come to the party or else she will reveal to everybody that he was the one that sent the video of Blair confessing her love. Dan makes this lie that he felt a spark with Serena and needs Blair to make Serena come to Nate’s party. A fool for romance, Blair obliges hoping the two would get back together.
Meanwhile, Charlie Rhodes/Ivy is back in town eager to speak with Lily about something. The only person Charlie runs into is Georgina. Georgina is trying to get Charlie to dish out gossip but Charlie doesn’t have any except that Blair and Louis signed a prenuptial agreement. In Georgina’s quest to take down Blair, she decides to look into the prenuptial. Georgina finds out that if Blair defaults in any way during her and Louis marriage, Blair’s family would go bankrupt just to pay off the dowry. This makes Georgina hungry for some drama.
At the party where everybody assembles yet again, Blair and Dan start talking about how to get Serena back. Blair gets all sentimental talking about how wonderful Dan has been to her these past few months and that anybody would love him for what he has done. It looks like the two might kiss until Gossip Girl sends a text message to Dan telling him to Kiss Blair already. Dan is flustered and is on the hunt to find GG.
Meanwhile, Blair tells Serena that she should go find Dan to rekindle their feelings for one another.
In another part of the room, Charlie/Ivy ends up at the party also as her mission to find Lily winds up at the Empire. Of course Lola/the real Charlie is also at that party catering. Lola spots Charlie/Ivy because they knew each other from Florida. They were in the same acting class. The two briefly catch up until Nate butts into their conversation. At this point Charlie/Ivy awkwardly and abruptly excuses her and Nate makes fun of Lola/real Charlie about actually knowing somebody very influential at his party…Charlotte Rhodes.
Meanwhile, downstairs of the Empire hotel Chuck Bass is wallowing in his drinks. Dan’s book agent recognizes him and because she is lonely, she throws herself onto him. However, Chuck is not in the mood for some alone time and declines her offer to make out in his bedroom.
Dan continues to try to find GG and it leads to none other than Georgina. Dan can’t believe he finally knows who GG really is. Georgina leaves once Blair comes finding Dan. Blair asks Dan if his intentions with Serena are true or if it is just a ruse to get Serena’s hopes up and then knocking her down. She continues to ask him what would really make him happy. Finally, Dan kisses Blair and Blair kisses right back! Of course, Georgina pops her head back in and starts taking pictures and Serena is also in the doorway witnessing their kiss.
Serena is heartbroken and declares their friendship over. Dan chases Georgina to try to get rid of the picture. Georgina tells Dan about the importance of the picture as it would make Blair’s family poor because of the dowry. Dan decides not to oust Georgina as GG and Georgina decides not to leak the photo of Dan and Blair kissing because she wants to hold onto her post as GG for a little bit longer. She does however show the picture Chuck.
Chuck is upset and decides to bang Dan’s book agent anyway.
Lola/real Charlie is confused about Ivy/fake Charlie and decides to look her up on Facebook and add her as a friend.
Fake Charlie never makes it to Lilly. Instead, she makes it to the Hamptons where Grandma Rhodes is ailing from sickness and it is fake Charlie who has been by her side.
Dan finally knows that Blair does have an inkling of feelings for him. However, Blair makes it clear that whatever it is that is between them, she would never do anything to hurt Serena. Will Dan and Blair ever get a shot at having a real relationship? Only time will tell.
Happy Valentine’s Day Upper East Side isn’t it a wonderful celebration of all kinds of love, good and bad.