As the summer draws to a close, Serena and Nate pretend they are in a relationship. Blair returns from abroad with a new man and Jenny sneaks an invite to a much-coveted Hamptons' White Party.

Blair is over the moon about dating royalty, but a scheming Chuck has other plans for her. Nate learns the downside to having an affair while Serena and Dan keep their recent hook up a secret.

Blair and Chuck question the lack of passion in their relationships. Nate struggles with his feelings for Vanessa and his relationship with Catherine. Serena and Dan are forced to confront their issues.

Blair and her minions decide to befriend the new girl, Amanda, in order to sabotage her possible new relationship with Dan. Vanessa discovers a scandalous secret about Catherine.

In the midst of Fashion Week, a furious Blair decides to sabotage her mother's show. Meanwhile, Dan starts hanging out with Chuck.

After they get into a fight, Serena decides to get even with Blair. Dan discovers that none of his recommendation letters for Yale were ever submitted.

Blair seeks revenge against Vanessa. Serena rebels at Lily and Barts housewarming party. Dan and Jenny discover a secret that Nate has been hiding.

Jenny befriends a young model, who encourages Jenny to explore her wild side. Serena meets an artist, and realizes they have an instant chemistry. Blair attempts to seduce Chuck.

Serena uncovers a secret Aaron has been keeping from her. Blair agrees to babysit the 15-year-old daughter of a Yale donor. Meanwhile, Jenny and Agnes plan a fashion show.

Blair tries break up her mother and her new man. Jenny moves in with Agnes. Serena learns something that may derail her relationship with Aaron and Dan interviews Bart Bass for an article.

Blair is offended when her mom's new boyfriend ruins her Thanksgiving traditions. Lily attempts to strengthen the frail bond between Rufus and Jenny. Eric discovers a secret about Bart.

As the annual Snowflake Ball approaches, Blair and Chuck make a bet that they can find the perfect date for one another. Aaron's ex-girlfriend expresses interest in Dan, creating mixed feelings for Serena.

A sudden and tragic event impacts the lives of everyone on the Upper East Side.

Chuck's uncle Jack arrives in the city. Blair focuses on being accepted into the most prestigious ladies club in the city and Jenny returns to Constance Billard.

Bart's will reveals what will come of the Bass empire. Meanwhile, Dan uncovers Rufus and Lily's secret, putting him in an awkward position.

The students are stressed out as they find out who was accepted for early admission to Yale. Chuck finds an unlikely ally in his feud with Jack.

Blair comes up with a devious plan to take down her new teacher. Chuck has no recollection of what happened to him when he wakes up in a hotel.

The Constance Billard and St. Jude seniors put on a production of "The Age of Innocence." Chuck finds help in an unlikely friend.

Devastated by the turn her life has taken, Blair opts for a wild lifestyle instead of her perfect Waldorf life. Vanessa tries to convince Nate that he needs to move on after his mother's family abandoned them.

Serena throws Jenny a sixteenth birthday party, but things spin out of control. Vanessa agrees to help Chuck. Rufus searches for a way to cover Dan's college tuition.

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.

Georgina returns to the Upper East Side. Chuck and Nate's relationship is at a crossroads. Serena's relationship with Gabriel gets more complicated.

Blair puts pressure on Georgina to help her in a scheme. The rivalry between Nate and Chuck reaches a boiling point. Lily makes a secret plan to help Rufus.

In a flashback, Lily runs away to Los Angeles, reconnecting with her parents. Back in present day, Blair and Nate attend prom together, but the evening doesn't turn out as planned.

Gossip Girl decides to liven things up at graduation by sending out a shocking and damaging email blast in the midst of the commencement ceremony. Lily and Rufus struggle to repair their relationship.