Season 5

Episode 1: Yes Than Zero

Serena loves her new job in Hollywood, but makes a costly misstep when she tries to impress her boss. Chuck and Nate arrive in Los Angeles as the last stop of their Lost Summer trip, joining Serena at a glamorous Hollywood Hills party, where Nate meets a sexy older woman. Blair and Louis return from Monaco and begin planning their royal wedding, but when Louis refuses to stand up to his family and support Blair's choices, his weakness threatens their relationship. A magazine is planning to run an excerpt of Dan's book until an unlikely ally steps in to help him kill the story.

Episode 2: Beauty and the Feast

Nate reconnects unexpectedly with Diana, who offers him an exciting new opportunity, as Serena forces Charlie to decide which world she wants to embrace. Dan seeks out Chuck's help to stop the publication of his book, but discovers it is Chuck who needs the help. Blair's future sister-in-law, Beatrice, arrives from Monaco, but her motives with Blair may be more than just to get acquainted.

Episode 3 - The Jewel of Denial

Nate has to decide whether to cross moral lines at Diana's request. Dan is trying to figure out who is publishing his book, and seeks help to stop it but ends up in the spotlight anyway. Chuck helps Dan and Dan helps Chuck break through. Meanwhile, Serena and Charlie return to the Upper East Side.

Episode 4 - Memoirs of an Invisible Dan

After much thought, Dan finally decides to gather everyone and reveal the truth about his book, hoping that they will support him at his book party. Meanwhile, Blair and Louis struggle after Louis reads Dan's book. Diana has some incriminating information about one of Nate's friends and uses it to her advantage.

Episode 5 - The Fasting and the Furious

In the celebration of Yom Kippur with family and friends, Blair and Louis have a power struggle with Louis's family. Serena's boss asks her to choose between her new job and Dan. Diana prepares to debut the New York Spectator, but a surprise delays the launch and Diana expects Nate to help her.

Episode 6 - I Am Number Nine

Blair makes a competition to fill her bridesmaids spots in her upcoming royal wedding. Meanwhile Nate is tired of keeping the secret of his relationship to Diana, so he decides to use Charlie to make Diana jealous. Serena's boss wants to acquire the film rights to Dan's book, so Serena has to put her personal feelings aside to close the deal.

Episode 7 - The Big Sleep No More

The gang attend a performance of Punchdrunk's provocative theater experience, "Sleep No More," which translates into masks, anonymity and some surprising romantic twists by the end of the evening. Meanwhile, Diana's target is Serena in her quest to ruin Gossip Girl. Dan is out on his book tour, but things are not as they appear to be to his friends and family.

Episode 8 - All The Pretty Sources

Serena plans a dream bridal shower for Blair, but she has to plant false information about the event so that Blair does not find out. Chuck and Dan spend the day together to forget that they were not invited to Blair's shower. Nate and Serena find something about Diana and struggle with how and when to use it.

Episode 9 - Rhodes To Perdition

Lily, Charlie and Serena anticipate a party thrown in CeCe's honor. Nate takes on a new role at the Spectator, and his first big job is of someone he knows very well. Meanwhile, Blair turns to an unlikely source for help.

Episode 10 - Riding In Town Cars With Boys

Lily throws Charlie a party to officially introduce her to New York society. Meanwhile, Charlie’s ex-boyfriend, Max, throws a wrench into Charlie’s future as an Upper East Side princess.

Episode 11 - The End of The Affair?

Through a series of emotional flashbacks, Blair reveals to Serena what really happened in the aftermath of her tragic car accident with Chuck. Meanwhile, Nate discovers information about the accident that suggests possible foul play. Lily is worried by Charlie's long absence and decides to hire a private detective to track her down. Vera Wang makes a cameo as herself at Blair's dress fitting. Penn Badgley and Matthew Settle also star. Michael Grossman directed the episode written by Sarah Goodman.

Episode 12 - Father and the Bride

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. Kelly Rutherford and Matthew Settle also star. Amy Heckerling directed the episode written by Peter Elkoff.

Episode 13 - G.G.

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 (guest star Hugo Becker), the return of Georgina Sparks (guest star Michelle Trachtenberg) might make the royal affair a royal disaster. Kelly Rutherford and Matthew Settle also star. Mark Piznarski directed the episode written by executive producer Joshua Safran.

Episode 14 - The Backup Dan

Blair must make a difficult decision about her future, the consequences of which could hurt those she loves most. Serena takes the blame for an incident with Gossip Girl in order to protect someone she loves. Georgina smells the scent of scandal and decides to follow its trail.

Episode 15 - Crazy, Cupid, Love

It's Valentine's Day on the Upper East Side and Blair can't resist playing cupid for someone she loves. Georgina is intent on stirring up more drama, so she decides to crash Nate's Valentine's Day party. Meanwhile, Serena is shocked by something she witnesses at the party.

Episode 16 - Cross Rhodes

Dan feels honored when he learns that Upright Citizen's Brigade is performing excerpts from his book, Inside. Blair tries to prove Serena's suspicions wrong in order to save their friendship. On her way out of town, Ivy ends up on a collision course with the van der Woodsens.

Episode 17 - The Princess Dowry

Blair thinks Cyrus may have found a potential loophole in her prenup. Chuck and Georgina partner up in a scheme, but it has an unpredictable outcome. Meanwhile, a family crisis brings William van der Woodsen back to the Upper East Side.

Episode 18 - Con-Heir

Chuck invites Jack to town to thank him for saving his life, but finds the trip doesn't go exactly as planned. Blair and Dan attempt to consummate their new relationship -- but unexpected roadblocks get in their way. Meanwhile, Ivy finds an unlikely ally in William in her quest to be accepted on the Upper East Side, and Nate is hopeful a new investor will save his newspaper.

Episode 19: It Girl, Interrupted

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 for advice about his past, and Diana Payne's return to The Spectator starts a power struggle with Nate.

Episode 20 - Salon of the Dead

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 (founders of The Oracle Club). 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.

Episode 21: Despicable B

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.

Episode 22 - Raiders of the Lost Art

Chuck, Nate, Blair, Serena and Lola (guest star Ella Rae Peck) team up to uncover what they think is an explosive secret between Diana and Jack (guest star Desmond Harrington). Meanwhile, Dan is offered a prestigious fellowship in Rome for the summer.

Episode 23: The Fugitives

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.

Episode 24 - The Return of the Ring

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?