The students first learn that Serena van der Woodsen, once the Upper East Side's most notorious party girl, 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.
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.
In the wake of the scandalous Kiss on the Lips party, Serena (Blake Lively) receives an icy cold reception from her best friend Blair (Leighton Meester), who reveals that she knows Serena slept with her boyfriend, Nate (Chace Crawford), before mysteriously running off to boarding school.
As if it couldn't get any chillier, Serena decides to take Dan (Penn Badgley) to arch-enemy Chuck's (Ed Westwick) fundraiser brunch at The Palace, and Jenny (Taylor Momsen) seeks advice from Blair, who realizes she may have something to gain by allowing Jenny into her inner circle.
As the Upper East Side teens from Constance Billard and St. Jude's prepare for a much-anticipated visit from the Ivy League representatives, Blair (Leighton Meester) uncovers a scandalous secret about Serena (Blake Lively) that may not remain a secret much longer. Dan (Penn Badgley) has his heart and future set on the coveted usher position for the Dartmouth rep, only to be beat out by Nate (Chace Crawford), who has no interest in the school despite pressure from his controlling father, The Captain (Sam Robards).
Meanwhile, Jenny (Taylor Momsen) bonds with Serena's younger brother, Eric (Connor Paolo), and Rufus (Matthew Settle) must swallow his pride and ask Lily (Kelly Rutherford) for a favor to help his son, Dan.
Blair (Leighton Meester) is thrilled when her mother, Eleanor (Margaret Colin), 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 (Blake Lively) moves into the spotlight and Blair is finds herself back in Serena's shadow.
Meanwhile, Serena and Dan (Penn Badgley) are reminded once again that they come from two very different worlds, and Nate (Chace Crawford) and Chuck (Ed Westwick) indulge in a boys' weekend to blow off steam after Ivy Week.
Dan (Penn Badgley) makes elaborate plans to impress Serena (Blake Lively) on their first official date. The same night, Jenny (Taylor Momsen) is invited to the infamous Blair Waldorf (Leighton Meester) sleepover and finds herself in a high stakes game of "truth or dare."
Meanwhile, when Lily (Kelly Rutherford) discovers that Eric (Connor Paolo) is missing from his treatment center, she finds herself seeking help from her ex-boyfriend, Rufus (Matthew Settle).
Dan (Penn Badgley) is torn between two girls when his childhood friend, Vanessa (Jessica Szohr), returns home and declares her feelings for him, just as he and Serena (Blake Lively) are trying to figure out what they mean to each other. At the infamous masked ball, Blair (Leighton Meester) sends Nate (Chace Crawford) on a scavenger hunt, but Nate is ultimately still distracted by his feelings for Serena. Although Blair makes it perfectly clear that outsiders are not welcome, a disguised Jenny (Taylor Momsen) and Dan sneak into the ball.
Finally, Lily (Kelly Rutherford) asks Rufus (Matthew Settle) to accompany her to an Eleanor Waldorf (Margaret Colin) event in order to make Bart Bass (Robert John Burke) jealous. "America's Next Top Model" winner CariDee English makes a cameo as Bart Bass' date.
After surviving the on-again/off-again nature of their new relationship, Serena (Blake Lively) and Dan (Penn Badgley) finally acknowledge they are crazy about each other, despite their polar opposite worlds that constantly threaten to pull them apart.
Chuck (Ed Westwick) contemplates investing in a burlesque club in the hopes of making his hard-to-please father, Bart (guest star Robert John Burke), proud of him. Nate (Chace Crawford) confronts his father, Captain (guest star Sam Robards), about the drugs he found in the house, but his father denies having a problem.
Jenny (Taylor Momsen) discovers a secret her father, Rufus (Matthew Settle), and mother, Alison (guest star Susan Misner), have been keeping from her. Finally, Blair (Leighton Meester) is once again devastated by Nate's actions after Jenny reveals that Nate kissed her by accident thinking she was Serena.
Devastated by the current state of her relationship with Nate (Chace Crawford) and still dealing with the guilt from her recent indiscretion, Blair (Leighton Meester) puts on a happy face for her 17th birthday party and attempts to hide the truth from her friends. Hoping to ease the tension between Serena (Blake Lively) and Vanessa (guest star Jessica Szohr), Dan (Penn Badgley) takes Vanessa to Blair's party so the girls can have some bonding time, but this only ends up making Serena more uncomfortable. Jenny (Taylor Momsen) brings her mom (guest star Susan Misner) home for a surprise visit, but Rufus (Matthew Settle) may not be ready to forgive and forget. Nate's parents (guest stars Sam Robards and Francie Swift) ask him to make a huge sacrifice in an effort to salvage his father's business as he faces charges of embezzlement and fraud. Ed Westwick and Kelly Rutherford also star.
When Dan (Penn Badgley) hears that Serena (Blake Lively) and her family are spending Thanksgiving alone at The Palace, he naively invites them to spend the holiday with his family, creating an uncomfortable situation for Rufus (Matthew Settle) and Lily (Kelly Rutherford) whose children are unaware of their complicated romantic history.
Meanwhile, Blair's (Leighton Meester) emotions spiral out of control when she learns that her father isn't coming home for Thanksgiving. Nate (Chace Crawford) spends the holiday with his mom (guest star Francie Swift) and dad (guest star Sam Robards), but their awkward dinner quickly goes from bad to worse.
The annual Cotillion Ball is about to take place. Blair is not going with Nate, but she finds herself being featured in The New York Times and is enjoying her secret affair with Chuck. Serena is not going, so her grandmother, CeCe, shows up to change her mind. Jenny volunteers for the ball and Lily takes her under her wing. But the night of The Cotillion is the night of Alison's first art opening, and Rufus and Alison say Jenny cannot attend the ball. Jenny decides to defy them both. Refreshed by Blair's newly buoyant attitude, Nate asks her to The Cotillion and she says yes, which makes Chuck jealous. CeCe tells Lily and Serena that she is sick and her last dying wish is to see Serena go to the ball, and she wants Serena to go with Carter Baizen. CeCe insults Dan and offers to pay Rufus off to convince Dan not to go with Serena. Dan learns of this and tells Serena that he does not think very highly of CeCe, which results in a huge fight between them. Serena decides to go to the ball with Carter. Chuck manipulates Nate into thinking Carter is having an affair with Blair, so Nate punches Carter at the ball.
When Blair's (Leighton Meester) father, Harold (guest star John Shea), comes home for the holidays with an unexpected guest -- his boyfriend, Roman (guest star William Abadie) -- Blair finds it difficult to hide her disappointment and hatches a plan to get rid of Roman for good.
Jenny (Taylor Momsen) and Vanessa (Jessica Szohr) help Serena (Blake Lively) plan the best Christmas surprise ever for Dan (Penn Badgley), who may have a surprise of his own in mind for Serena. Chuck (Ed Westwick) texts Blair that Nate (Chace Crawford) has joined him in Monaco, worrying Blair that Chuck may disclose the details of their hook-up.
Rufus (Matthew Settle) refuses to remain the understanding husband any longer after Alison's (guest star Susan Misner) former lover calls the house.
Serena (Blake Lively), Blair (Leighton Meester), Nate (Chace Crawford), Chuck (Ed Westwick) and their entourage break into the school swimming pool for a 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 (Penn Badgley), who isn’t sure he’s ready to take the fall for someone else and risk his future. Vanessa (Jessica Szohr) is working on a documentary project about private schools and accidentally captures Blair and Chuck discussing their affair. Lily (Kelly Rutherford) contemplates telling Rufus (Matthew Settle) how she really feels about him. Taylor Momsen also stars. The episode was directed by Tony Whamby and written by Lenn K. Rosenfeld.
Gossip Girl takes pleasure in reporting that Serena van der Woodsen (Blake Lively) was spotted buying pregnancy tests. Of course, on the Upper East Side, the truth is often even juicier and more scandalous than the gossip, and this time is no exception. Leighton Meester, Penn Badgley, Chace Crawford, Taylor Momsen, Ed Westwick, Kelly Rutherford and Matthew Settle also star.
Having been recently dethroned as Queen Bee in the last episode by Gossip Girl, with an assist from scheming "little J" (Taylor Momsen), Blair (Leighton Meester) hesitantly returns to school with the support of her BFF, Serena (Blake Lively).
Meanwhile, Serena struggles to adjust to her new living arrangements with her future step-brother, Chuck (Ed Westwick), while receiving disturbing packages from an unknown sender. Jenny's drive to be popular hits an all-new time high when she does something illegal to fit in with her new Upper East Side friends.
Serena's Upper East Side world is turned upside down when her former partner in all things bad, Georgina Sparks (guest star Michelle Trachtenberg), returns to Manhattan to stir up trouble and Serena's past. When Dan (Penn Badgley) notices that Serena seems preoccupied he jumps to the conclusion that it must have something to do with Serena's new roomie and soon-to-be step-brother, Chuck (Ed Westwick). Nate (Chace Crawford) finds romance with the last person he was expecting to connect with, Vanessa (Jessica Szohr). Jenny (Taylor Momsen) meets a new guy, Asher Hornsby (guest star Jesse Swenson), who just might be her ticket to permanent popularity. Finally, Blair (Leighton Meester) hatches a secret plan to sabotage her biggest rival, Nelly Yuki (guest star Yin Chang).
Georgina (guest star Trachtenberg) informs Serena (Blake Lively) that she is prepared to reveal damaging information from Serena's past, but no one is prepared for what Georgina does next.
Blair (Leighton Meester) and Jenny (Taylor Momsen) escalate their "popularity war" by spreading scandalous rumors about each other through Gossip Girl. Dan (Penn Badgley) witnesses Jenny's new boyfriend, Asher (guest star Jesse Swenson), cheating on her, but Jenny refuses to listen to her brother's warning.
Rufus (Matthew Settle) goes to Lily (Kelly Rutherford) for advice on how to handle Jenny's recent out-of-character behavior.
As a result of Georgina (guest star Michelle Trachtenberg) revealing the true reason that Serena (Blake Lively) fled Manhattan for boarding school, Serena falls back into her old habits and Blair (Leighton Meester), Nate (Chace Crawford) and Chuck (Ed Westwick) must put their complicated feelings for each other aside to help their friend. Unfortunately, Serena is too ashamed to share the truth with Dan (Penn Badgley), leaving him only to assume the worse about his girlfriend.
Rufus (Matthew Settle) is thrilled when his band is invited to perform at a Rolling Stone-sponsored concert, but Lily (Kelly Rutherford) is the last person on earth he expects to see at the performance, especially since her wedding rehearsal dinner is the same night. Lisa Loeb and famous cake designer Sylvia Weinstock appear in the episode as themselves.
With her best friend Serena's (Blake Lively) life and reputation on the line, Blair (Leighton Meester) decides to take matters into her own hands in dealing with the manipulative and evil Georgina Sparks (guest star Michelle Trachtenberg). With Rufus (Matthew Settle) never far from her thoughts, Lily (Kelly Rutherford) prepares for her wedding day which is destined to be the Upper East Side's social event of the year. Serena finally pours out her heart and the truth about her past to Dan (Penn Badgley), but will it prove to be too late to save their relationship?
Heiress and model Lydia Hearst guest stars in the episode as Amelia, Lily's interior decorator.