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 the picture, Serena turns to Nate to help her get through a difficult situation. As a favor to Chuck, Jenny agrees to hang out with Damien, the son of an ambassador who is staying at Chuck's hotel, but the experience proves to be a lot more intriguing than she expected.

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 Robinson. Jenny is forced to choose between her relationship with Eric and her new role as Queen Bee. Rufus gets Lily into the Halloween spirit.

Jenny 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. Meanwhile Dan and Vanessa try to convince Olivia to stay in NY by showing her the "true college experience". Leighton Meester's new single "Somebody to Love" is featured in the episode, along with performance from Plastiscines.

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.

Lily, Charlie and Serena eagerly anticipate the Studio 54 party being thrown in CeCe’s honor. Nate takes on a new role at the Spectator, but his first big story turns out to be about someone he knows all too well. Blair turns to an unlikely person for help.

Feeling the pressure to make her first Waldorf Designs fashion show a success, Blair must rely on help from an unlikely source, but some unexpected scheming causes a scandal on the runway. Serena discovers that befriending Steven’s daughter Sage is trickier than she thought, especially when she is forced to put her issues with Blair aside to make Sage happy. Nate publishes Dan’s first serialized article causing a stir and producing a serious threat. Meanwhile, Chuck begins to look into the clue that Amira left behind, which may help uncover what Bart is hiding.

Blair feels like her Upper East Side status might be slipping away and devises a plan to assure that doesn’t happen. Meanwhile, Lily throws a family gathering – including William, Carol and Lola – in an attempt to prove the van der Woodsen family is as united as ever. Finally, Nate digs into Diana’s past and is surprised by what he discovers.

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?

Several of our favorite Upper East Siders attend a performance of Punchdrunk’s provocative theater experience, “Sleep No More,” which translates to masks, anonymity and some surprising romantic twists by the end of the evening. Meanwhile, Diana sets her sights on Serena in her quest to ruin Gossip Girl. Dan is out on his book tour, but things aren’t exactly as they appear to his friends and family.

Trying to prove herself in adult society, Serena hosts the Central Park Conservancy’s big gala, of which she is now the newest Board Member, and she and Nate both learn something shocking about their significant others. Blair prepares to debut her new fashion line, but a rival from her past holds the key to her future. With the help of Georgina, Dan lands some meetings with publishers, but he must decide if he is willing to sacrifice his integrity in order to get his work published. Meanwhile, Chuck tries to persuade Amira to help him look into his father’s past, even if it means jeopardizing Lily and Bart’s relationship.

After Blair and Serena get into a catfight, Serena decides to get even with Blair, who has always dreamed of attending Yale, by ditching her plans to visit Brown, and instead accepting the Dean of Yale's personal invitation to visit the school. After discovering that none of his recommendation letters for Yale were ever submitted, Dan frantically tries to figure out a way to salvage his chances of getting into the school. While on the Yale campus, Chuck is kidnapped by a group of Skull and Bones members and Nate hooks up with a co-ed.

Blair comes up with a devious plan to take down her new teacher, Rachel. Chuck has no recollection of what happened to him when he wakes up in a hotel. Nate and Vanessa try to help Chuck fill in the missing pieces of his night. Meanwhile Dan and Serena try to keep their relationship together as Rufus and Lily grow even closer.

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.

After much deliberation, Dan decides to gather Serena, Blair, Nate, Chuck, Rufus and Lily to reveal the truth about his book in the hope that they will support him at his book party. Meanwhile, Blair and Louis hit a crises point after Louis reads Dan's book. Diana learns incriminating information about one of Nate's friends and uses it to her advantage.

Serena is hard at work planning a dream bridal shower for Blair, but it should come as no surprise that Serena has to plant some false information about the shower in order to keep Blair from finding out all the details. Chuck and Dan decide to spend the day together to distract themselves from the fact that they didn’t make the invite list for Blair’s shower. Nate and Serena find a silver bullet in Diana’s war against Gossip Girl, but struggle about whether to use it or not.

Blair prepares to celebrate her upcoming royal wedding with a bachelorette party, but others scheme behind her back to make this a night to remember. After discovering the truth behind Chuck and Blair’s car accident, Nate joins forces with a surprising ally to gather the evidence. Serena and Dan pretend to be dating again to protect someone close to them.

The much-anticipated 100th episode will open with a musical dream sequence featuring Serena, Blair and all the men in their lives. Also, while Chuck wrestles with the reality that Blair is about to walk down the aisle with Prince Louis, the return of Georgina Sparks might make the royal affair a royal disaster.

Serena decides she is ready to relinquish the spotlight and sets out to make a reluctant Lola the next “It Girl” of the Upper East Side, starting with modeling at a Kiki de Montparnasse lingerie show. Meanwhile, Chuck reaches out to Blair or advice about his past, and Diana Payne’s return to The Spectator starts a power struggle with Nate.

To celebrate their official coming out as a couple, Blair and Dan host a glamorous British-themed Salon, including guests Julian Tepper and Jenna Gribbon Lola lands the audition of a lifetime, but Gossip Girl may have other plans for the Upper East Side’s latest It Girl. Meanwhile, Lily and Rufus disagree over the best way to handle the Ivy situation, and Serena and Diana face-off over secrets they both would prefer remain secrets.

Blair enlists Serena to be her stand-in at an important meeting when Blair finds herself needing to be in two places at the same time. Meanwhile, Ivy and Lola team up to help Chuck with a personal vendetta, and Nate makes a decision about the future with Diana Payne.

After a brief encounter abroad, Chuck and Blair make a promise to each other about their relationship, which leaves them once again apart. Dan, with some help from an unlikely ally, Georgina, is writing a scathing tell-all book that can only mean trouble. As the sole head of The Spectator, Nate is making his own decisions and is ready to go up against Gossip Girl. As word spreads that Serena is missing, the gang bands together to find her and are shocked by what they find.

Jenny has a new young model friend, named Agnes, who encourages Jenny to explore her wild side, and also to confront Eleanor Waldorf who is planning to steal Jenny's designs in order to pass them off as her own. Meanwhile, Serena and Dan attend Rufus' latest art opening as friends, but then Serena meets an artist, named Aaron Rose, and the evening gets a little uncomfortable for Dan. Elsewhere, Blair attempts to seduce Chuck, but he proves to be tougher than she ever imagined. Also, Jenny begins to have a mutual feelings with Nate as he's staying with her, Dan, and Rufus while searching for a place to live.

Blair sets out on a mission to break up her mother and Cyrus Rose, her new man. Jenny moves in with Agnes as the two continue with their plans for their own fashion line. As Serena continues to fall for Aaron, she learns something that may derail their relationship forever while Dan interviews Bart Bass for an article for New York Magazine.

Chuck, Jack and Lily come together for the reading of the will which reveals what will come of the Bass empire. Rufus and Lily's relationship is put on hold as Rufus searches for the child he never knew he had. Meanwhile, Dan does some digging of his own and uncovers Rufus and Lily's secret, putting him in an awkward position.

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.