5×01 Yes, Then Zero
Spotted – Our favorite Upper East Siders on the West Coast! Plus, pregnancy mystery solved, Royal Wedding in the works and guest star Elizabeth Hurley
Serena (Blake Lively) loves her new job in Hollywood, but makes a costly misstep when she tries to impress her boss (guest star Michael Michele). Chuck (Ed Westwick) and Nate (Chace Crawford) 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 (guest star Elizabeth Hurley). Blair (Leighton Meester) and Louis (guest star Hugo Becker) 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 (Penn Badgley) book until an unlikely ally steps in to help him kill the story. Kaylee DeFer and Matthew Settle also star. Mark Piznarski directed the episode written by executive producer Joshua Safran.
5×02 Beauty And The Feast
Elizabeth Hurley Guest Stars in a multi-episode arc for Season Five – Episode is set in both New York and Los Angeles
Nate (Chace Crawford) reconnects unexpectedly with Diana (Elizabeth Hurley), who offers him an exciting opportunity. Serena (Blake Lively) forces Charlie (Kaylee DeFer) to decide which world she wants to embrace. Dan (Penn Badgley) seeks out Chuck’s (Ed Westwick) help to stop the publication of his book, but discovers it is Chuck who needs the help. Blair’s (Leighton Meester) future sister-in-law, Beatrice (guest star Roxane Mesquida), arrives from Monaco, but her motives with Blair may be more than just to get acquainted. Matthew Settle also stars. Mark Piznarski directed the episode written by co-executive producer Sara Goodman.
5×03 The Jewel of Denial
Elizabeth Hurley Guest Stars in a multi-episode arc for Season Five – Episode features a Jenny Packham Fashion Show
Nate (Chace Crawford) must decide whether to cross moral lines at Diana’s (Elizabeth Hurley) request. Dan (Penn Badgley) has figured out who is publishing his book, and seeks help to stop it, but he ends up in the spotlight anyway. Chuck (Ed Westwick) helps Dan come to terms with his fate, just as Dan continues to try to help Chuck break through his emotional block. Serena (Blake Lively) and Charlie (Kaylee DeFer) return to the Upper East Side from California. Leighton Meester, Kelly Rutherford and Matthew Settle also star. Larry Shaw directed the episode written by Amanda Lasher.
5×04 Memoirs of an Invisible Dan
Elizabeth Hurley Guest Stars in a multi-episode arc and Tate Donovan Directs
After much deliberation, Dan (Penn Badgley) decides to gather Serena (Blake Lively), Blair (Leighton Meester), Nate (Chace Crawford), Chuck (Ed Westwick), Rufus (Matthew Settle) and Lily (Kelly Rutherford) to reveal the truth about his book in the hope that they will support him at his book party. Meanwhile, Blair (Leighton Meester) and Louis (guest star Hugo Becker) hit a crises point after Louis reads Dan’s book. Diana (Hurley) learns incriminating information about one of Nate’s friends and uses it to her advantage. Kaylee DeFer also stars. Tate Donovan directed the episode written by Amy B. Harris.
5×05 The Fasting and the Furious
Yom Kippur at the Waldorfs – Elizabeth Hurley guest stars in a multi-episode arc
In the midst of celebrating Yom Kippur with family and friends, Blair (Leighton Meester) and Louis (guest star Hugo Becker) find themselves in a power struggle with Louis’ family. Serena’s (Blake Lively) boss (guest star Michael Michele) puts Serena in the awkward position of choosing between her new job and her relationship with Dan (Penn Badgley). Diana (Hurley) prepares to debut the New York Spectator, but an unfortunate last-minute surprise delays the launch and Diana expects Nate (Chace Crawford) to do whatever it takes to save the day. Ed Westwick, Kaylee DeFer, Kelly Rutherford and Matthew Settle also star. Joe Lazarov directed the episode written by Peter Elkoff.
5×06 I Am Number Nine
Blair auditions her potential bridesmaids
Blair (Leighton Meester) makes all of her former minions and Charlie (Kaylee DeFer) compete to secure the coveted bridesmaid spots in her upcoming royal wedding. Nate (Chace Crawford) is tired of keeping his relationship with Diana (guest star Elizabeth Hurley) a secret, so he decides to use Charlie to make Diana jealous. Serena’s (Blake Lively) boss (guest star Michael Michele) is determined to acquire the film rights to Dan’s (Penn Badgley) book, so Serena must put her personal feelings about Dan and the book aside in order to close the deal. Ed Westwick and Matthew Settle also star. Andy Wolk directed the episode written by Jake Colburn.
5×07 The Big Sleep No More
Gossip Girl film at the much-talked-about theater experience “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 (guest star Elizabeth Hurley) sets her sights on Serena (Blake Lively) in her quest to ruin Gossip Girl. Dan (Penn Badgley) is out on his book tour, but things aren’t exactly as they appear to his friends and family. Leighton Meester, Chace Crawford, Ed Westwick, Kaylee DeFer, Kelly Rutherford and Matthew Settle also star. Andy Wolk directed the episode written by Dan Steele.
5×08 All The Pretty Sources
Serena plans a dream bridal shower for Blair
Serena (Blake Lively) is hard at work planning a dream bridal shower for Blair (Leighton Meester), 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 (Ed Westwick) and Dan (Penn Badgley) 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 (Chace Crawford) and Serena find a silver bullet in Diana’s (guest star Elizabeth Hurley) war against Gossip Girl, but struggle about whether to use it or not. Kaylee DeFer, Kelly Rutherford and Matthew Settle also star. Cherie Nowlan directed the episode written by Austin Winsberg.
5×09 Rhodes to Perdition
Episode directed by Andrew McCarthy
Lily (Kelly Rutherford), Charlie (Kaylee DeFer) and Serena (Blake Lively) eagerly anticipate the Studio 54 party being thrown in CeCe’s (guest star Caroline Lagerfelt) honor. Nate (Chace Crawford) 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 (Leighton Meester) turns to an unlikely person for help. Penn Badgley, Ed Westwick and Matthew Settle also star. Andrew McCarthy directed the episode written by Natalie Krinsky.
5×10 Riding in Town Cars with Boys
Lily introduces Charlie to New York Society
Lily (Kelly Rutherford) throws Charlie (Kaylee DeFer) a party to officially introduce her to New York society. Meanwhile, Charlie’s ex-boyfriend, Max (guest star. Brian J. Smith), throws a wrench into Charlie’s future as an Upper East Side princess. Dan (Penn Badgley) decides it may be time to tell Blair (Leighton Meester) the truth about his feelings for her. Chace Crawford, Ed Westwick and Matthew Settle also star. Vince Misiano directed the episode written by Amanda Lasher.
5×11 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.
5×12 Father and the Bride
Blair’s bachelorette party – episode directed by Amy Heckerling (“Clueless”)
Blair (Leighton Meester) 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 (Ed Westwick) and Blair’s car accident, Nate (Chace Crawford) joins forces with a surprising ally to gather the evidence. Serena (Blake Lively) and Dan (Penn Badgley) 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.
5×13 G.G.
OMG! Gossip Girl hits 100 episodes!
The much-anticipated 100th episode will open with a musical dream sequence featuring Serena (Blake Lively), Blair (Leighton Meester) and all the men in their lives (Penn Badgley, Chace Crawford, Ed Westwick and Hugo Becker). Also, while Chuck (Ed Westwick) 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.
5×14 The Backup Dan
Blair struggles with a decision about her future
Blair (Leighton Meester) must make a difficult decision about her future, the consequences of which could hurt those she loves most. Serena (Blake Lively) takes the blame for an incident with Gossip Girl in order to protect someone she loves.. Georgina (Michelle Trachtenberg) smells the scent of scandal and decides to follow its trail. Penn Badgley, Chace Crawford, Ed Westwick, Kelly Rutherford and Matthew Settle also star. David Warren directed the episode written by Matt Whitney.
5×15 Crazy, Cupid Love
Nate throws a Valentine’s Day Bash – St. Vincent performs
It’s Valentine’s Day on the Upper East Side and Blair (Leighton Meester) can’t resist playing cupid for someone she loves.. Georgina (Michelle Trachtenberg) is intent on stirring up more drama, so she decides to crash Nate’s (Chace Crawford) Valentine’s Day party. Meanwhile, Serena (Blake Lively) is shocked by something she witnesses at the party. Penn Badgley, Ed Westwick, Kaylee DeFer, Kelly Rutherford and Matthew Settle also star. Matt Penn directed the episode written by Austin Winsberg.
5×16 Cross Rhodes
Dan’s book is showcased by Upright Citizen’s Brigade
Dan (Penn Badgley) feels honored when he learns that Upright Citizen’s Brigade is performing excerpts from his book, Inside. Blair (Leighton Meester) tries to prove Serena’s (Blake Lively) suspicions wrong in order to save their friendship.. On her way out of town, Ivy (Kaylee DeFer) ends up on a collision course with the van der Woodsens. Chace Crawford, Ed Westwick, Kelly Rutherford and Matthew Settle also star. John Terlesky directed the episode written by Amy B. Harris.
5×17 The Princess Dowry
Billy Baldwin (“William Van Der Woodsen”) returns – Andrew McCarthy directs the episode
Blair (Leighton Meester) thinks Cyrus (Wallace Shawn, who does not appear in the episode) may have found a potential loophole in her prenup. Chuck (Ed Westwick) and Georgina (Michelle Trachtenberg) partner up in a scheme, but it has an unpredictable outcome. Meanwhile, a family crisis brings William van der Woodsen (Baldwin) back to the Upper East Side. Blake Lively, Penn Badgley, Chace Crawford, Kaylee DeFer, Kelly Rutherford and Matthew Settle also star. Andrew McCarthy directed the episode written by Jake Coburn.
