Blair has to decide between meeting Chuck at the Empire State Building or risking their future together. A gossip about Dan causes problems for Serena and Nate. Meanwhile, Georgina Sparks (Michelle Trachtenberg) returns to the Upper East Side with and agenda.

When things get tense between Rufus and Will, Serena chooses to stand behind her father, while at the Rufus is made to feel like an outsider in his own family. Meanwhile, Jenny deliberately shares information with Will that may ultimately destroy Lily and Rufus’ marriage. After many failed attempts, Chuck makes one last grand gesture to reconcile with Blair, hoping she will finally accept the fact that they are destined to be together.

Will’s return to the Upper East Side continues to stir up problems for Serena, Lily and his long-standing rival, Rufus. Serena and Jenny’s relationship is strained as a result of Jenny’s deception. Blair spends time on the Columbia campus and realizes where she truly belongs…. Dan learns that Vanessa has been keeping yet another secret from him.

Serena’s father (William Baldwin) visits Manhattan unexpectedly; Nate and Serena continue to have relationship issues; Dan gets upsetting news.

Dorota asks Chuck and Blair to be a part of her wedding; Serena secretly meets with Carter; Rufus discovers that Lily has been lying about her whereabouts.

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

Chuck finds himself once again at odds with his uncle, Jack Bass. Eleanor puts Blair in charge of making sure her latest fashion show is a huge success with an important client. Rufus attempts to get Jenny back on track by volunteering to have her help with Eleanor’s fashion show, but the opportunity takes a big turn for the worse when Jenny learns that Agnes will be one of the models.

Despite being grounded, Jenny continues to see Damien who tells Jenny that he wants to have sex with her. Lily tells Rufus the big secret she has been keeping from him even though she knows it’s a huge risk. Dan and Vanessaexplore a new stage of their friendship. Chuck is forced to make an extremely difficult decision about his hotel.

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

Nate and Serena decide to explore the boundaries of their friendship. Blair suspects that Chuck is having problems forgetting about the woman he saw at his father’s grave. Jenny agrees to accompany Damien to a State Dinner but is unaware that he needs her help with a drug exchange. Vanessa and Dan attempt to move past the awkwardness of Dan’s confession of love. Rufus returns from a ski trip and tries his best to avoid Lily.

A year after his father’s death, Chuck deals with an issue from the past, and another car accident occurs on the Upper East side. Meanwhile, Dan and Vanessa face the new complexities in their friendship; and Jenny gets accused of assaulting a classmate

Thanksgiving dinner becomes uncomfortable for Serena when Lily invites Trip and his wife to attend. Meanwhile, Blair thinks her mom is keeping a secret from her; Rufus discovers Lily has been lying about Cece; and Vanessa has a fight with her mother

Hoping to impress the elitist theater kids at NYU, Blair calls in a favor to land a private concert with the hottest musical performer of the year, Lady Gaga.

Not satisfied with just being Queen of Constance Billard, Jenny sets her sights on becoming the Queen of all the Upper East Side by landing the hottest escort for Cotillion.

Olivia says something she regrets during her appearance on Jimmy Fallon’s talkshow and tries to keep Dan from finding out. With election day around the corner, Nate suspects his grandfather will stop at nothing to get Trip elected to congress. In the midst of another feud with Serena, Blair befriends a new “it” girl and takes her to an election night party at Chuck’s hotel, hoping to make Serena jealous.

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 infamous sex scenes with co-star and real-life boyfriend at the time, Patrick...

Vanessa (Jessica Szohr), hoping to finally win her mother Gabriela’s (guest star Gina Torres) approval, desperately vies with Blair (Leighton Meester) for the honor of delivering the freshman toast at NYU, but at what price? Dan (Penn Badgley) invites Olivia (guest star Hilary Duff) to meet Rufus (Matthew Settle) and Lily (Kelly Rutherford), which leads to all sorts of problems for the new couple. Serena (Blake Lively) and Nate (Chace...

Lily and Rufus move their wedding forward to the next day. Chuck uncovers Carter’s secret. Georgina traps Dan and Vanessa into one of her schemes.

It’s the first day of school at Constance Billard which means it’s also time for Jenny to take her rightful place as the new Queen Bee. Unfortunately for Jenny, Blair is more than happy to intervene when news reaches her that she may be needed back at Constance. Lily returns home to Rufus and her family to find that things are definitely not as she left them. A famous movie actress, Olivia Burke (Hilary Duff), enrolls at NYU – and is...

It’s a face-off between Chuck and Blair when they both want to bid on the same item at Sotheby’s. Meanwhile, Serena suspects that Carter may have return to his old habits, while Georgina takes an interest in Dan, and Vanessa suspect something is not right with Scott.