Gossip Girl reports that Serena van der Woodsen was seen buying pregnancy tests. Of course, on the Upper East Side, the truth is often even juicier and more scandalous than the gossip. Nate finds out about Blair and Chuck's affair. And when everyone else finds out what happened Blair's life comes crashing down. Meanwhile, Dan struggles to tell Serena those three special words.

Having been recently dethroned as Queen Bee, Blair returns to school with the support of Serena to find she is still on the outs with her old friends. Dan visits his mother over spring break, and when he returns, Jenny is on the verge of becoming a full-fledged member of the A-List crowd. Jenny must go to dangerous and even illegal lengths to fit in. Serena struggles to adjust to living with Chuck, and receives disturbing packages from an unknown sender.

Serena's world descends into chaos when a former friend, the evil Georgina Sparks returns to town. Nate connects with the last person he expected, Vanessa. Blair hatches a plan to sabotage her biggest rival, Nelly Yuki. Meanwhile Serena goes out with Georgina, but things get so bad that Serena thinks someone spiked her non-alcoholic drink. Jenny develops a crush on a dog-walker, Asher Hornsby, who might be her ticket to permanent popularity.

Georgina informs Serena that she can reveal a deep dark secret from Serena's past, but no one is prepared for what Georgina does next. Blair and Jenny's power struggle continues when each of them start spreading scandalous rumors about each other on Gossip Girl. Dan sees Jenny's new beau, Asher, cheating on her, but Jenny won't listen to him. Rufus goes to Lily for advice on how to handle Jenny's new behavior. Serena tries to confront Georgina, but she leaves before Serena has a chance. After this, Serena says that she and Georgina are not friends.