Serena throw’s Jenny an 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 desesperation agrees to help Chuck with a scheme having to do with Blair and Nate. Rufus tries to figure out how to cover Dan’s Yale tuition, when he learns that Dan will not receive financial aid.

Devastated by recent events, Blair explores her dark side; Lily and Rufus decide to be completely honest with each other. Vanessa receives an interesting offer by Nate’s grandfather and she has a hard time refusing it

Serena develops a crush on the director of the school play; Blair gets devastating news about her future; Dan and Rachel have a hard time staying away from each other.