The season began in Los Angeles when a re-energized Chuck and Nate decided to pay Serena a visit. Chuck has a newfound philosophy and says "yes" to everything, even death defying stunts. Serena continues to work on the movie set, and is offered a full-time job at the end of the episode. Nate begins an affair with an older woman, Diana Payne, who may have an ulterior motive for being with Nate. Back in New York, Dan learns that Vanessa has published one chapter of his novel, and Blair continues to plan her wedding to Louis, and she also learns she is pregnant. After realizing she still had feelings for Chuck, Blair and Chuck decide to go away together, but their car crashes. As a result of the crash Blair loses her baby, Chuck nearly dies, and Blair eventually marries Louis. The season also focuses on Nate running an online gossip site NYSpectator, Blair and Dan's friendship turning into a relationship, Chuck's quest to find his real parents which leads him to discover that his father, Bart, is still alive, and the effects of CeCe's death on Lily and her marriage to Rufus. At the end of the season, Blair makes a choice between Dan and Chuck, and Lily makes a choice between Rufus and Bart. Serena is seen leaving town while Dan decides to write a new book about the Upper East Side, with the help of Georgina.

Season 5 Episode 1 - Yes, Then 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. Air Date : 26th-Sep-2011  Read More

Season 5 Episode 2 - Beauty and the Feast

Nate reconnects unexpectedly with Diana, who offers him an exciting opportunity. 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. Air Date : 3rd-Oct-2011  Read More

Season 5 Episode 3 - The Jewel of Denial

Nate must decide whether to cross moral lines at Diana’s request. Dan has figured out who is publishing his book, and seeks help to stop it, but he ends up in the spotlight anyway. Chuck helps Dan come to terms with his fate, just as Dan continues to try to help Chuck break through his emotional block. Serena and Charlie return to the Upper East Side from California. Air Date : 10th-Oct-2011  Read More

Season 5 Episode 4 - Memoirs of an Invisible Dan

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. Air Date : 17th-Oct-2011  Read More

Season 5 Episode 5 - The Fasting and the Furious

In the midst of celebrating Yom Kippur with family and friends, Blair and Louis find themselves in a power struggle with Louis' family. Serena's boss puts Serena in the awkward position of choosing between her new job and her relationship with Dan. Diana prepares to debut the New York Spectator, but an unfortunate last-minute surprise delays the launch and Diana expects Nate to do whatever it takes to save the day. Air Date : 24th-Oct-2011  Read More

Season 5 Episode 6 - I Am Number Nine

Blair makes all of her former minions and Charlie compete to secure the coveted bridesmaid spots in her upcoming royal wedding. Nate is tired of keeping his relationship with Diana a secret, so he decides to use Charlie to make Diana jealous. Serena's boss is determined to acquire the film rights to Dan's book, so Serena must put her personal feelings about Dan and the book aside in order to close the deal. Air Date : 7th-Nov-2011  Read More

Season 5 Episode 7 - The Big Sleep No More

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. Air Date : 14th-Nov-2011  Read More

Season 5 Episode 8 - All The Pretty Sources

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. Air Date : 21st-Nov-2011  Read More

Season 5 Episode 9 - Rhodes To Perdition

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. Air Date : 28th-Nov-2011  Read More

Season 5 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. Dan decides it may be time to tell Blair the truth about his feelings for her. Air Date : 5th-Dec-2011  Read More

Season 5 Episode 11 - The End of The Affair?

Blair's flashbacks reveal the fallout of her and Chuck's car accident, which Nate realizes may have been caused by foul play. Meanwhile, Lily gets a private eye to locate Charlie; and Vera Wang makes an appearance at Blair's bridal-dress fitting. Air Date : 16th-Jan-2012  Read More

Season 5 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. Air Date : 23rd-Jan-2012  Read More

Season 5 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, the return of Georgina Sparks might make the royal affair a royal disaster. Air Date : 30th-Jan-2012  Read More

Season 5 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. Air Date : 6th-Feb-2012  Read More

Season 5 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. Air Date : 13th-Feb-2012  Read More

Season 5 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. Air Date : 20th-Feb-2012  Read More

Season 5 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. Air Date : 27th-Feb-2012  Read More

Season 5 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. Air Date : 2nd-Apr-2012  Read More

Season 5 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 or advice about his past, and Diana Payne’s return to The Spectator starts a power struggle with Nate. Air Date : 9th-Apr-2012  Read More

Season 5 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 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. Air Date : 16th-Apr-2012  Read More

Season 5 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. Air Date : 23rd-Apr-2012  Read More

Season 5 Episode 22 - Raiders of the Lost Art

Chuck, Nate, Blair, Serena and Lola team up to uncover what they think is an explosive secret between Diana and Jack. Meanwhile, Dan is offered a prestigious fellowship in Rome for the summer. Air Date : 30th-Apr-2012  Read More

Season 5 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. Air Date : 7th-May-2012  Read More

Season 5 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? Air Date : 14th-May-2012  Read More