Chuck and Blair’s relationship is faced with the most difficult decision they have ever faced as a couple. Serena plans a surprise birthday party for Nate, but Jenny tries to sabotage her. Meanwhile, Dan and Vanessa’s relationship hits a bump in the road.

Jack Bass is back in NY and Chuck finds himself at odds with his uncle. Eleanor puts Blair in charge of making sure her fashion show is a huge success with an important client. Rufus tries to get Jenny to be more good by volunteering to help in Eleanor’s fashion show, but it takes a turn for the worse when Jenny finds out that Agnes is one of the models.

Despite being grounded, Jenny continues to see Damien who pressures her to sleep with him. Lily tells Rufus the big secret she has been keeping from him even though she knows it’s very risky. Meanwhile, Dan and Vanessa explore the new stage of their friendship, while Chuck is forced to make a very difficult desicion about his hotel.

Rufus and Lily suspect something bad about Jenny’s and Damien relationship. Chuck learns more about the woman at the cementery who may or may not be his mother. Meanwhile, Dan and Vanessa struggle with the awkwardness of dating other people.

On the anniversary of Bart Bass death, Chuck has to deal with some issues from the past and a car accident disturbs the Upper East Side. Meanwhile, Dan and Vanessa tried to stay in their complicated friendship no matter what. Jenny is accused of beating a classmate, and Eric has to decide which story to beleive.

Blair bid to find out what her Mother is hiding backfires. Vanessa gets into a fight with her mom and ends up at the Humphreys. Rufus is hurt when he discovers Lily has been lying to him. Chuck divulges some news that could ruin a friend to Nate. Jenny finds tries to get even with Eric after learning the truth.

Trying to impress NYU theater kids, Blair uses her contacts to get a private concert with today’s hottest performer, Lady Gaga. Dan and Olivia sign up to write and star in an NYU play, based on an idea by Blair and directed by Vanessa. Meanwhile, Serena turns to Nate for help in a dificult situation, now that Blair is not there. As a favor to Chuck, Jenny agrees to hang out with Damien, an ambassador’s son staying in Chuck’s hotel, and the experience turned out to be more intriguing than what she thought.

enny wants to be the Queen Bee of not only Constance but of all the Upper East Side, as she lands the hottest escort for the Cotillion. Leighton Meester’s new single “Somebody to Love”, is featured in the episode, along with performace from Plastiscines.

Olivia says something she regrets during her appearance on Jimmy Fallon’s (Fallon playing himself) talkshow and tries to keep Dan from finding out. With election day around the corner, Nate and Vanessa suspects that William will stop at nothing to get Tripp (guest star Aaron Tveit) elected to congress. In the midst of another feud with Serena, Blair befriends who she believes to be the new “it” girl and takes her to Tripp’s election party, hoping to make Serena jealous. Vanessa becomes upset with Nate because of his schemes during the election.

It’s Halloween on The Upper East Side and in need of publicity for his new hotel, Chuck decides to move up his club’s opening and enlists Serena’s help to get the word out to her celebrity clients. Feeling left out of the planning, Blair attempts to win Chuck’s approval by secretly helping him with a problem concerning opening night. Dan is unnerved when he finally watches one of Olivia’s (guest star Hilary Duff) infamous sex scenes with co-star and real-life boyfriend at the time, Patrick Robinson (guest star Simon Miller). Jenny is forced to choose between her relationship with Eric and her new role as Queen Bee. Meanwhile Rufus gets Lily into the Halloween spirit.