The fifth season of the American teen drama television series Gossip Girl premiered on The CW on September 26, 2011, and concluded on May 14, 2012, consisting of 24 episodes.

Kaylee DeFer was upgraded to a series regular status in her roles as Serena's cousin, Charlie Rhodes, and aspiring actress/con artist Ivy Dickens.

Blair Waldorf receives life-changing news and is still stuck in the love triangle between Chuck Bass and Louis Grimaldi, and begins seeking comfort from the unlikeliest of people, Dan Humphrey.

Nate reconnects with the mysterious Diana Payne (Elizabeth Hurley), a woman whom he had a fling with in Los Angeles who offers him a job opportunity to work at her newspaper, The New York Spectator.

Worrying that her identity will be revealed, Ivy decides to start forging her own path by becoming a part of New York's social scene as Charlie.

Unknowingly, Nate is persuaded by the ruthless maneater Diana to cross moral lines while interviewing a couple at the Jenny Packham fashion show.

Elsewhere, a very reluctant Blair decides she does not want to learn who the father of her unborn child is, but is later seen telling Chuck that she is pregnant with Louis' baby, but adds "Part of me wished it was yours".

Even Rufus becomes angry and alienated with Dan when he says he had never regretted leaving the music industry to have a family, until upon reading the book, which portrays him as marrying Lily just for money.

While her stepfather and mother, Cyrus and Eleanor, decide to throw a Yom Kippur dinner party to celebrate, Sophie and Beatrice try to get Blair to accept a series of conditions following the marriage.

As Rufus and Lily continue to avoid talking with Dan over his book, Chuck connects with an attractive therapist who rebuffs his advances and seems to see right through his character for who he really is.

Blair tries out three of her former minions to see if they are worthy to be her bridesmaids, and Charlie willingly teams up with the group in order to seek out a story, where she proves herself to be more than a match for the mean girls.

Several of the group attend a performance of Punchdrunk's provocative theater experience, "Sleep No More", which involves masks, anonymity and some surprising romantic twists by the end of the evening.

Meanwhile, Diana sets her sights to snag Serena a job at The Spectator as part of her twisted quest to ruin Gossip Girl's website.

Serena and Lily prepare Charlie for her first debutante ball to welcome her into New York high society, but the vindictive Max is determined to reveal Charlie/Ivy's secret by any means necessary.

Nate learns that his grandfather, William van der Bilt, owns the majority of stock shares at The Spectator and he influenced Diana to hire him.

After Max's pleas to both Serena and Nate about Charlie's real identity fall on deaf ears, he runs into Tripp van der Bilt, whom he tells Ivy’s story to.

Meanwhile, Serena decides that she has to tell Dan how she feels while Nate unknowingly meets the real Charlie Rhodes working as a waitress at the reception.

With the help of a group of informants, Georgina decides to crash Nate's Valentine's Day party which is being held at the Empire Hotel, while Chuck does not feel in the holiday spirit and falls into his old habits.

Georgina Sparks decides to leave her post at Gossip Girl to her loyal but incompetent husband, Phil, and crash the wake to stir up more trouble.

However, this is all a ruse perpetrated by Georgina herself, who sends a photo of Blair and Dan kissing to Gossip Girl and the Waldorfs are once again threatened with responsibility of paying the dowry and declaring bankruptcy.

Blair feels like her Upper East Side status might be slipping away and devises a plan to assure that does not happen by upstaging Dan at a publishers’ gathering.

Lola receives her share of the van der Woodsen estate from her biological father, William, and also learns that Lily intentionally sabotaged Carol's defense in court to keep her imprisoned as well as destroyed Ivy's case in order to keep Cece's wealth all for herself.

Nate receives CCTV footage from Diana Payne of the real Gossip Girl (a hooded masked figure) stealing Serena's laptop on the night of Bart's return.

Footage containing the World Trade Center have been omitted by films and TV shows such as Sex and the City and The Sopranos to honor individuals who died in the attacks.

Head of Warner Bros. Television, Peter Roth was also confident that the show will return, stating, "I can't really say at this point, but I would hope and expect that there would be at least another year—if not years—to come.

Kaylee DeFer was upgraded to series regular status, while Taylor Momsen and Jessica Szohr exited the show, though they were both invited back as guest stars.

"[34] Former Lost actor Marc Menard joined the cast in the role of Father Cavalia, a handsome priest from Monaco who will preside over Blair's wedding.

[41] Brian J. Smith, known for his role on Stargate Universe, had been cast as a love interest for Serena while she is in Los Angeles and would appearing on the show as Max, an aspiring chef.

[46] Aaron Tveit, who previously portrayed Nate's cousin Tripp van der Bilt in the third season, returned to the show for a multi-episode arc.

Back in New York, Blair learns that planning a royal wedding can be stressful, especially with a baby on the way, and Dan discovers the consequences of writing candidly about his closest friends.