Original air date: 09/19/2007 Runtime: 42:30 min. The privileged prep school teens on Manhattan's Upper East Side first learn that Serena van der Woodsen (Blake Lively, "The Sisterhood of the Traveling Pants") is back in town the way they learn all the important news in their lives -- from the blog of the all-knowing albeit ultra- secretive Gossip Girl. No one knows Gossip Girl's identity, but everyone in this exclusive and complicated vicious circle relies on her website and text messages for the latest scoop. Even Serena's closest friend, Blair Waldorf (Leighton Meester, "Entourage"), is surprised to find that Serena has suddenly ended her self-imposed exile to boarding school and returned to Manhattan. Once the Upper East Side's most notorious party girl, Serena's reasons for returning are mysterious, although they may have something to do with her younger brother Eric (Connor Paolo, "Alexander"). Whatever the reasons, the change in Serena is obvious, especially to Blair, whose friendship with Serena has always been competitive and difficult.
Original air date: 09/26/2007 Runtime: 39:22 min. In the wake of the scandalous Kiss on the Lips party, Serena receives an ice-cold reception from her best friend, Blair, who reveals that she knows Serena slept with her boyfriend, Nate, before mysteriously running off to boarding school. Serena decides to take Dan to archenemy Chuck's fundraiser brunch at The Palace. And Jenny seeks advice from Blair, who realizes she may have something to gain by allowing Jenny into her inner circle.
Original air date: 10/03/2007 Runtime: 41:32 min. As the Upper East Side teens from Constance Billard and St. Jude's prepare for a much-anticipated visit from Ivy League representatives, Blair uncovers scandalous information about Serena that may not remain a secret much longer. Dan has his heart -- and future -- set on serving in the coveted usher position for the Dartmouth representative. But he is beat out by Nate, who has no interest in the school, despite pressure from his controlling father, the Captain (recurring guest star SAM ROBARDS). Meanwhile, Jenny bonds with Serena's younger brother, Eric (recurring guest star CONNOR PAOLO). And Rufus must swallow his pride and ask Lily for a favor to help his son, Dan.
Original air date: 10/10/2007 Runtime: 42:04 min. Blair is thrilled when her mother chooses her to be the new face of her clothing line. However, Blair's happiness soon turns to feelings of betrayal and jealousy when Serena moves into the spotlight, and Blair finds herself back in Serena's shadow. Meanwhile, Serena and Dan are reminded once again that they come from two very different worlds. And Nate and Chuck indulge in a boys' weekend to blow off steam after Ivy Week.
Original air date: 10/17/2007 Runtime: 39:54 min. Dan makes elaborate plans to impress Serena on their first official date. On the same night, Jenny is invited to the infamous Blair Waldorf sleepover and finds herself in a high-stakes game of Truth or Dare. Meanwhile, when Lily discovers that Eric (recurring guest star CONNOR PAOLO) is missing from his treatment center, she seeks help from her ex- boyfriend, Rufus.
Original air date: 10/24/2007 Runtime: 42:22 min. Dan is torn between two girls when his childhood friend, Vanessa (recurring guest star JESSICA SZOHR), returns home and declares her feelings for him, just as he and Serena are trying to figure out what they mean to each other. At her infamous masked ball, Blair sends Nate on a scavenger hunt, but he is still distracted by his feelings for Serena. Although Blair makes it perfectly clear that outsiders are not welcome, a disguised Jenny and Dan sneak into the ball. Meanwhile, Lily asks Rufus to accompany her to an event hosted by Blair's mother in order to make Chuck's father, who brought a model ("America's Next Top Model" winner CARIDEE ENGLISH) as his date, jealous.
Original air date: 11/07/2007 Runtime: 42:18 min. After surviving their relationship's on-again/off-again genesis, Serena and Dan finally acknowledge that they are crazy about each other, despite their polar-opposite worlds that constantly threaten to pull them apart. Chuck contemplates investing in a burlesque club, hoping to make his hard-to-please father, Bart (recurring guest star ROBERT JOHN BURKE), proud of him. Nate confronts his father, the Captain (recurring guest star SAM ROBARDS), about the drugs he found in the house, but the Captain denies having a problem. Jenny discovers a secret that her father, Rufus, and mother, Alison (SUSAN MISNER), have been keeping from her. And Blair is once again devastated by Nate's actions after Jenny reveals that Nate accidentally kissed her, thinking she was Serena.
Original air date: 11/28/2007 Runtime: 41:41 min. When Dan finds out that Serena and her family are celebrating Thanksgiving alone, he naïvely invites them to spend the holiday with his family, creating an uncomfortable situation for Rufus and Lily, whose children are unaware of their complicated romantic history. Meanwhile, Blair's emotions spiral out of control when she learns that her father isn't coming home for Thanksgiving. Nate marks the holiday with his mom and dad, but their awkward dinner quickly goes from bad to worse.
Original air date: 12/05/2007 Runtime: 42:10 min. Serena has absolutely no intention of attending the upcoming Debutante Ball, until her grandmother, CeCe (guest star CAROLINE LAGERFELT - "All the King's Men," "Nash Bridges"), announces that Serena must attend. Unfortunately, CeCe does not find Dan to be the "suitable escort" she had in mind for Serena, and makes her opinion heard loud and clear, causing a riff between Serena and Dan. Blair and Nate, now officially broken up, decide to go to the ball together as friends; however, Nate becomes jealous when he begins to suspect that Blair may already be seeing someone else. Meanwhile, Jenny finds herself torn between attending her mother’s (recurring guest star SUSAN MISNER) art opening or following her dreams of going to the Debutante Ball, even though the latter is against her parents’ wishes. And Rufus finally learns the real reason Lily broke up with him all those years ago.
Original air date: 12/19/2007 Runtime: 42:36 min. When Blair’s father, Harold (recurring guest star JOHN SHEA), comes home for the holidays with an unexpected guest -- his boyfriend, Roman (guest star WILLIAM ABADIE - "Entourage," "The O.C.," "The Pink Panther") -- Blair finds it difficult to hide her disappointment and hatches a plan to get rid of Roman for good. Meanwhile, Jenny and Vanessa (recurring guest star JESSICA SZOHR) help Serena plan the best Christmas surprise ever for Dan; Dan, in turn, may be thinking of his own surprise for Serena. And when Chuck texts Blair from Monaco saying that Nate has joined him there, Blair worries that Chuck may disclose the details of their hook-up. Back in Brooklyn, Rufus refuses to remain the understanding husband after a former lover of Alison's (recurring guest star SUSAN MISNER) calls the house.
Original air date: 01/02/2008 Runtime: 42:28 min. The gang breaks into the school swimming pool for an impromptu night of fun, but when a member of their group nearly drowns, the school threatens to expel the person responsible for the break-in. Everyone agrees to keep a secret pact and say nothing, but it ultimately creates major tension between Serena and Dan, who isn’t sure he’s ready to risk his future and take the fall for someone else. Meanwhile, Vanessa (recurring guest star JESSICA SZOHR), who is working on a documentary project about private schools, accidentally captures Blair and Chuck discussing their affair, and Lily contemplates telling Rufus how she really feels about him.
Original air date: 01/09/2008 Runtime: 42:11 min. Gossip Girl takes pleasure in reporting that Serena van der Woodsen has been spotted buying a pregnancy test, and the word spreads like wildfire. Of course, on the Upper East Side, the truth is often juicier and more scandalous than the gossip, and this time is no exception.
Original air date: 04/21/2008 Runtime: 40:23 min. Having recently been dethroned as Queen Bee in the last episode by Gossip Girl, with an assist from scheming "little J," Blair hesitantly returns to school with the support of her BFF, Serena. Meanwhile, Serena struggles to adjust to her new living arrangements with her future stepbrother, Chuck, while receiving disturbing packages from an unknown sender. And Jenny's drive to be popular hits a new all-time high when she does something illegal to fit in with her new Upper East Side friends.
Original air date: 04/28/2008 Runtime: 41:32 min. Serena's Upper East Side world is turned upside down when her former partner in all things bad, Georgina Sparks (recurring guest star MICHELLE TRACHTENBERG - "Buffy the Vampire Slayer," "Six Feet Under"), returns to Manhattan to stir up trouble -- and Serena's past. When Dan notices that Serena seems preoccupied, he jumps to the conclusion that it must have something to do with Serena's new roommate and soon-to-be stepbrother, Chuck. Meanwhile, Nate finds romance with the last person he was expecting to connect with, Vanessa, and Jenny meets a new guy, Asher Hornsby (recurring guest star JESSE SWENSON), who just might be her ticket to permanent popularity. Plus, Blair hatches a secret plan to sabotage her biggest rival, Nelly Yuki (guest star YIN CHANG - "Law & Order: Criminal Intent," "Six Degrees").
Original air date: 05/05/2008 Runtime: 42:19 min. Georgina (recurring guest star MICHELLE TRACHTENBERG) informs Serena that she is prepared to reveal damaging information from Serena's past, but no one is ready for what Georgina does next. Blair and Jenny escalate their "popularity war" by spreading scandalous rumors about each other through Gossip Girl. Dan witnesses Jenny's new boyfriend, Asher (recurring guest star JESSE SWENSON), cheating on her, but Jenny refuses to listen to her brother's warning. Rufus goes to Lily for advice on how to handle Jenny's recent out-of-character behavior. Plus, one of the Upper East Side teens reveals that he is gay.
Original air date: 05/12/2008 Runtime: 42:24 min. Georgina (recurring guest star MICHELLE TRACHTENBERG) reveals the true reason that Serena fled Manhattan for boarding school, and Serena quickly falls back into her old habits. Blair, Nate and Chuck must put their complicated feelings for each other aside to help their friend. Unfortunately, Serena is too ashamed to share the truth with Dan, leaving him to assume the worst about his girlfriend. Meanwhile, Rufus is thrilled when his band is invited to perform at a Rolling Stone-sponsored concert, but Lily is the last person he expects to see at the performance, especially since her wedding rehearsal dinner is the same night. Recording artist LISA LOEB and famous cake designer SYLVIA WEINSTOCK appear as themselves.
Original air date: 05/19/2008 Runtime: 42:33 min. With Serena's life and reputation on the line, Blair -- as Serena's best friend -- decides to take matters into her own hands to deal with the manipulative and evil Georgina Sparks (recurring guest star MICHELLE TRACHTENBERG). Lily prepares for her wedding day, which is destined to be the Upper East Side's social event of the year, and finds that Rufus is never far from her thoughts. Serena finally opens up to Dan, pours out her heart and tells him the truth about her past, but will it prove to be too late to save their relationship? And Lily's interior decorator, Amelia (heiress and model LYDIA HEARST), makes a big impression on Chuck.