Gossip Girl decides to send a shocking email blast in the graduation ceremony of Constance Billard and St. Jude’s, pushing Serena to device a devious plan of attack. The Mean Girls Club challenge Jenny to succeed Blair as Queen Bee for next year. Lily and Rufus struggle with their relationship after Lily’s betrayal. As for the cliffhangers, Blair and Chuck finally…and Serena is shocked by…and Georgina decides to…and Dan, Nate and Vanessa unknowingly…

In a flashback to the 80s, we see a 17-year-old Lily who gets kicked out of boarding school and runs away to L.A., she there sees her parents, Rick and Cece, and her sister, Carol. Back in present day, Blair and Nate go to a prom together, but the night doesn’t turn out as planned and Chuck has a something to do with it. Serena and Lily don’t see eye-to-eye over Serena’s recent run-in with the law. And we see No Doubt perform as an 80’s band named “Snowed Out”.

Blair puts pressure on Georgina to making amends for her past bad behavior by helping her in an evil plan. The rivalry between Nate and Chuck over Blair reaches a boiling point. Lily makes a secret plan to help Rufus with Dan’s college tuition.

Georgina returns to the Upper East Side but it’s not the same Georgina we all knew, she’s changed. Chuck and Nate relationship is at a crossroad because of their mutual interest in Blair. Serena’s relationship with Gabriel get’s more complicated.

Serena returns from her trip to Spain with Poppy and Gabriel. Blair makes a secret deal with Nate’s grandfather. Dan takes a job to earn money for college.

Jenny’s kinda-not-sweet sixteen! Serena throws Jenny a small birthday party for her sweet sixteenth, but things get out of control when Poppy Lifton turns the birthday into a huge social event. Vanessa, in a moment of desperation, agrees to help Chuck with a scheme having to do with Blair and Nate. Meanwhile, Rufus tries to figure out how to cover Dan’s Yale tuition, when he learns that Dan will not receive financial aid.

Blair explores her dark side!!! Devastated by her current situations, Blair turns to her wild side, causing Serena and Chuck to have serious concerns about their friend. Vanessa convinces Nate that it may be time to forgive and forget when it comes to his mother’s Kennedyesque family, The Vanderbilts, who abandoned Nate and his mother when they needed them most. In an effort to be completely honest with each other, Lily and Rufus agree to share lists of their past lovers.

The Constance Billard and St. Jude seniors have the production of “The Age of Innocence”. Serena has a crush on the play’s director, Julian, and enlists Vanessa’s knowledge of theater to help her get the guy’s attention. Blair receives bad news about her future that leads her on a witch-hunt for the person responsible. Dan and Rachel agree to stay away from each other in the aftermath of being discovered as more than teacher and student, but find it impossible to keep that promise. Chuck find help on an unlikely friend, Carter Baizen.

Blair comes up with a devious plan to take down her new teacher, Rachel. Chuck has no recollection of what happened to him when he wakes up in a hotel. Nate and Vanessa try to help Chuck fill in the missing pieces of his night. Meanwhile Dan and Serena try to keep their relationship together as Rufus and Lily grow even closer.

Who will get in the Ivy League institution of their choice? The students find out who is worthy of an early admission to Yale. Serena connects with a new Shakespeare teacher, who has no clue about what is going to happen when she gives Blair the first B grade in her life. Chuck pairs up with an unlikely ally in his battle over Bass Industries. Nate and Vanessa have a romantic night at the opera.