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 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 [...]

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 [...]

Serena’s father visits Manhattan unexpectedly; Nate and Serena continue to have relationship issues and 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 [...]

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 Vanessa explore a new stage of their friendship. Chuck is forced to make an [...]

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 [...]

On the anniversary of Bart Bass’ death, Chuck wrestles with an issue from the past and a serious car accident rocks the Upper East Side. Dan and Vanessa attempt to navigate their newly complicated friendship. When Jenny is accused of beating up one of her classmates, Eric is faced with a tough dilemma.

It wouldn’t be Thanksgiving on the Upper East Side if there wasn’t a serving or two of some major drama for the holiday. Blair suspects her mom has been keeping a big secret from her, but it turns out to be something else entirely. Vanessa is supposed to spend Thanksgiving with her parents, but has [...]

Hoping to impress the elitist theater kids at NYU, Blair sets her sights on landing a private concert with the hottest musical performer of the year, Lady Gaga. Dan and Olivia sign up to write and star in a school play, based on an idea by Blair and directed by Vanessa. With Blair out of [...]

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. Nate and Chuck plot to help Serena and Blair repair their damaged friendship. Dan is upset when Olivia contemplates leaving school for a movie project.

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 [...]

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 [...]

Vanessa, hoping to finally win her mother Gabriela’s approval, desperately vies with Blair for the honor of delivering the freshman toast at NYU, but at what price? Dan invites Olivia to meet Rufus and Lily, which leads to all sorts of problems for the new couple. Serena and Nate team up to help Carter Baizen

Lily and Rufus decide to move up their wedding to the next day, but will someone or something come between them before they become man and wife? Chuck discovers a secret that Carter has been keeping from Serena. Dan and Vanessa are pulled into one of Georgina’s schemes. Blair is suspect of Bree and shares [...]

Jenny returns to Constance Billard 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 [...]

It’s an Upper East Side face-off when Blair and Chuck both set their sights on a particular item up for bid at Sotheby’s and the personal stakes are high. Serena suspects that Carter may be up to his old habits, Georgina takes an interest in Dan, and Vanessa begins to suspect that something isn’t quite [...]

Blair ends up with Georgina as as her roommate in the dorms at NYU. While Serena and Chuck come to blows, so she joins forces with Chuck’s enemy, Carter. Nate and Bree try to take their relationship up a gear despite the animosity between their families.

As the summer is drawing to a close, Blair and Chuck are madly in love and adjusting to their new “in a relationship” status, breaking all the traditional rules of dating as would be expected. Serena returns from her European adventure with many secrets to hide and a complicated relationship with Carter Baizen.