It's Ivy week for the Upper East Side teens of Constance Billiard and St. Jude's and the visiting representatives' arrival brings more than just college applications. Cut-throat rivalry is at its sharpest this week as the students compete for prestigious positions. Blair discovers a shocking but juicy secret about Serena and plots to drop the bomb at the best possible moment. Dan is sure that landing the coveted usher position with the Dartmouth rep will either make or break his future at the school. Unfortunately, it's Nate who nabs the position, despite total disinterest in the school. Meanwhile, Jenny gets closer to Serena's younger brother Eric and Rufus asks Lily for a favor.

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.

As the summer draws to a close in the Hamptons, Serena and Nate have everyone fooled into thinking they are a couple to cover up the fact that Nate has been hooking up with a married, older woman. Blair returns from abroad with a hot guy on her arm, making a very jealous Chuck question his decision to leave Blair stranded at the heliport. Dan has spent the summer assisting a famous author. While interning for Eleanor Waldorf's company, Jenny sneaks an invite to a much-coveted Hamptons' White Party at which Eric introduces her to socialite Tinsley Mortimer.

Devastated by the turn her life has taken, Blair opts for a wild lifestyle instead of her perfect Waldorf life, causing Chuck and Serena to become concerned. Vanessa tries to convince Nate that he needs to move on after his mother's family, the Vanderbilts, abandoned him and his mother. Trying to be honest with each other, Lily and Rufus both put together their lists of past relationships.

As summer draws to an end, Blair and Chuck continue to adjust to being in a relationship with one another. Serena returns from Europe with new secrets to hide and a new relationship with Carter Baizen. Nate also returns from vacationing and brings home a mysterious girl, Bree Buckley. Meanwhile, Rufus, Dan and Jenny spend the summer in the Hamptons and learn to adjust to the van der Woodsen's glamorous lifestyle

Blair must decide whether to meet Chuck at the top of the Empire State Building or risk losing their future together. A Gossip Girl gossip bomb involving Dan explodes Serena and Nate's relationship. Dorota and Vanya welcome their baby. Jenny hits rock bottom. Georgina returns to the Upper East Side...and she has an agenda.

As Lily awaits the consequences of her decision, William van der Woodsen, CeCe and Lily’s sister, Carol, come into town to support her and be part of a Taschen photo shoot on “modern royalty” in which the Rhodes family is participating. Unbeknownst to Carol, who has always chosen to keep her daughter Charlie far away from the Upper East Side, Charlie has followed her to New York to meet Serena and the rest of the family. Blair has an epiphany about her future, and grapples with the knowledge of whom she’s destined to be with.

When Gossip Girl goes after Blair as she’s never done before, Serena admits she may have unintentionally played an important role in Blair’s latest nightmare. Meanwhile, Nate invites Lola to move in with him, and Lily must make a big decision about the future of her marriage. Finally, by episode’s end, Blair will make a choice between the two men in her life…will it be Chuck or will it be Dan?