2x01 Summer Kind Of Wonderful
Gossip Girl Invades The Hamptons Guest Stars include author Jay McInerney, socialite Tinsley Mortimer and actress Madchen Amich — As the summer draws to a close in the Hamptons, Serena (Blake Lively) and Nate (Chace Crawford) have everyone fooled into thinking they are a couple to cover up the fact that Nate has been hooking up with a married older woman (guest star Amick) and Serena has been secretly mourning her break-up with Dan (Penn Badgley). Blair (Leighton Meester) returns from abroad with a hot guy on her arm (guest star Patrick Heusinger), making a very jealous Chuck (Ed Westwick) question his decision to leave Blair stranded at the heliport. Dan has spent the summer assisting a famous author (guest star McInerney), but decides to head to the Hamptons to see how things stand with Serena after a summer spent apart. While interning for Eleanor Waldorf’s company, Jenny (Taylor Momsen) sneaks an invite to a much-coveted Hamptons’ White Party at which Eric (Connor Paolo) introduces her to socialite Tinsley Mortimer. Matthew Settle also stars. J. Miller Tobin directed the episode written by Joshua Safran.
2x02 Never Been Marcused
Goodbye Hamptons... "Gossip Girl" is headed back to the Upper East Side Blair (Leighton Meester) is over the moon that she is dating royalty and has every intention of becoming a royal herself, but a scheming Chuck (Ed Westwick) has other plans for Blair and her new love, Marcus (guest star Patrick Heusinger). Serena (Blake Lively) and Dan (Penn Badgley) agree to keep their recent hook-ups a secret from their friends and family until they figure out what all this means for their relationship. Meanwhile, Nate (Chace Crawford) learns the downside to having an affair with a hot older woman, Catherine (guest star Madchen Amick), who also happens to be married. Taylor Momsen, Jessica Szohr and Matthew Settle also star. Michael Fields directed the episode written by executive producer Stephanie Savage.
2x03 The Dark Night
Chuck Loses His Mojo Serena (Blake Lively) and Dan (Penn Badgley) are forced to deal with their unspoken problems while trapped in an elevator during a citywide blackout. In a humorous twist, Blair (Leighton Meester) questions the lack of passion in her relationship with Marcus (guest star Patrick Heusinger), while at the same time Chuck (Ed Westwick)appears to have lost his “passion” for any woman other than Blair. Meanwhile, Nate (Chace Crawford) struggles between his feelings for Vanessa (Jessica Szohr) and his more-complicated-by-the-day relationship with Catherine (guest star Madchen Amick). Jenny (Taylor Momsen) risks losing her internship when Eleanor (Margaret Colin) catches Jenny critiquing one of the Eleanor Waldorf designs. Matthew Settle also stars. Janice Cooke directed the episode written by John Stephens.
2x04 The Ex-Files
There's a new girl in town When Serena (Blake Lively) notices that Dan (Penn Badgley) has been cozying up to the new girl in school, Amanda (guest star Laura-Leigh), the ever-loyal Blair (Leighton Meester) and her minions decide to befriend Amanda and sabotage her budding new romance with “lonely boy.” Vanessa (Jessica Szohr) discovers a scandalous secret about Catherine (guest star Madchen Amick) and enlists Blair’s scheming expertise to use the information to help Nate (Chace Crawford). Meanwhile, Lily (Kelly Rutherford) finds herself drawn back to her ex, Rufus (Matthew Settle), once again. Taylor Momsen and Ed Westwick also star. Jim McKay directed the episode written by Robby Hull.
2x05 The Serena Also Rises
Fashion Week Drama Designer Michael Kors and socialites Tinsley Mortimer and Cristina Cuomo make cameo appearances at Eleanor Waldorf's show. In the midst of Fashion Week, a furious Blair (Leighton Meester) learns that her mother, Eleanor (guest star Margaret Colin), at the suggestion of her protégé Jenny (Taylor Momsen), has given Serena (Blake Lively) and her new socialite friend, Poppy Lifton (guest star Tamara Feldman), front row seats to the Eleanor Waldorf show. Hurt once again by Serena’s popularity and her mother’s betrayal, Blair decides to sabotage the show. Meanwhile, Dan (Penn Badgley) starts hanging out with Chuck (Ed Westwick), but a walk on the dark side always has its risks and Dan learns that the hard way. Lily (Kelly Rutherford) learns a secret that her new husband, Bart (guest start Robert John Burke), has been keeping from her. Matthew Settle also stars. Patrick Norris directed the episode written by Jessica Queller.
2x06 New Haven Can Wait
Blair, Serena, Dan, Nate & Chuck pay a visit to Yale After Blair (Leighton Meester) and Serena (Blake Lively) get into a catfight, Serena decides to get even with Blair, who has always dreamed of attending Yale, by ditching her plans to visit Brown, and instead accepting the Dean of Yale’s personal invitation to visit the school. After discovering that none of his recommendation letters for Yale were ever submitted, Dan (Penn Badgley) frantically tries to figure out a way to salvage his chances of getting into the school. While on the Yale campus, Chuck (Ed Westwick) is kidnapped by a group of Skull and Bones members and Nate (Chace Crawford) hooks up with a co-ed. Taylor Momsen, Jessica Szohr, Kelly Rutherford and Matthew Settle also star. Norman Buckley directed the episode written by Alexandra McNally & Joshua Safran.
2x07 Chuck In Real Life
Blair convinces Chuck to seduce Vanessa Vanessa (Jessica Szohr) uses the scandalous picture of Catherine and Marcus to blackmail Blair (Leighton Meester) into being a nicer person, so Blair seeks revenge by enticing Chuck (Ed Westwick) to seduce Vanessa. Lily (Kelly Rutherford) and Bart (guest star Robert John Burke) throw an extravagant housewarming party and expect their children to make them proud in front of the attending press, but a rebellious Serena (Blake Lively) isn’t ready to play by their rules. Meanwhile, Dan (Penn Badgley) and Jenny (Taylor Momsen) discover a big secret that Nate (Chace Crawford) has been keeping from his friends. Matthew Settle also stars. Tony Wharmby directed the episode written by Lenn K. Rosenfeld.
2x08 Pret-a-Poor-J
Willa Holland )"The O.C.") guest stars and a new love interest for Serena (John Patrick Amedori) is introudeced Jenny (Taylor Momsen) befriends a young model, Agnes (guest star Willa Holland), who encourages Jenny to not only explore her wild side, but also confront her boss, Eleanor Waldorf (guest star Margaret Colin), who is attempting to “borrow” Jenny’s designs. Serena (Blake Lively) and Dan (Penn Badgley) agree to attend an art opening at Rufus’ (Matthew Settle) gallery as friends, but the outing gets a little uncomfortable after Serena meets an artist, Aaron Rose (guest star John Patrick Amedori), and realizes they have an instant chemistry. Blair (Leighton Meester) attempts to seduce Chuck (Ed Westwick), but it proves tougher than she ever imagined. Chace Crawford and Jessica Szohr also star. Vondie Curtis Hall directed the episode written by Amanda Lasher.
2x09 There Might Be Blood
Serena realizes that Aaron has been keeping a big secret from her Serena (Blake Lively) invites Aaron (guest star John Patrick Amedori) to be her guest at a charity gala honoring Lily and Bart (Kelly Rutherford and guest star Robert John Burke), but after discovering a secret that Aaron has been keeping from her she begins to question whether Aaron is the guy she thought he was. Hoping it will help her chances of getting into Yale, Blair (Leighton Meester) naively agrees to babysit the 15-year-old daughter of a prominent Yale donor, but the teenager proves to be more than a handful and Blair begins to suspect that the evening may actually wind up hurting her chances of getting into the college of her dreams. Meanwhile, Jenny (Taylor Momsen) and Agnes (guest star Willa Holland) plan a guerilla fashion show that will either launch Jenny’s star or ruin her chances of ever being accepted by the industry. Penn Badgley, Chace Crawford, Ed Westwick, Jessica Szohr and Matthew Settle also star. Michael Fields directed the episode written by Etan Frankel & John Stephens.
2x10 Bonfire of the Vanity
Wallace Shawn ("The Princess Bride") guest stars and Cyndi Lauper makes a cameo Blair (Leighton Meester) does not approve of the new man, Cyrus Rose (guest star Wallace Shawn), in her mother’s (guest star Margaret Colin) life, so she makes it her mission to break up the lovebirds by any means necessary. Jenny (Taylor Momsen) moves in with Agnes (guest star Willa Holland) as the friends move forward with their plans for a fashion line. Serena (Blake Lively) continues to fall for the new guy in her life, Aaron (guest star John Patrick Amedori), but she learns something about him that threatens to end things just as they are getting really good. Dan (Penn Badgley) decides to win the trust of Bart Bass (guest star Robert John Burke) in order to learn more about the man and possibly write an expose on him for Vanity Fair, but things get heated after Chuck (Ed Westwick) finds out the real reason Dan is spending so much time around his family. Matthew Settle also stars. David Von Ancken directed the episode written by Jessica Queller.
2x11 The Magnificent Archibalds
Thanksgiving on the Upper East Side Thanksgiving in the Waldorf household finds Blair (Leighton Meester) upset that her mom’s (Margaret Colin) new boyfriend, Cyrus (guest star Wallace Shawn), has decided to ruin all her favorite traditions, but that’s nothing compared to what’s coming next. Lily (Kelly Rutherford) finds herself trying to broker a peace treaty between Rufus (Matthew Settle) and Jenny (Taylor Momsen) who is prepared to cut off all communication with her father if she doesn’t get her way. Serena (Blake Lively) isn’t quite ready to come clean with Aaron (guest star John Patrick Amedori) about her complicated past, but Dan (Penn Badgley) ends up accidentally revealing a few tidbits of his own. Blair and Chuck (Ed Westwick) come to their friend’s aid when Nate (Chace Crawford) is once again forced to confront his father’s (guest star Sam Robards) abandonment. Finally, Eric (Connor Paolo) discovers a secret that Bart (Robert John Burke) has been keeping from Lily. Jessica Szohr also stars. Jean DeSegonzac directed the episode written by Joshua Safran.
2x12 It's a Wonderful Lie
The Annual Snowflake Ball For the annual Snowflake Ball, Blair (Leighton Meester) and Chuck (Ed Westwick) make a bet that they can find the ideal dates for each other. Aaron’s (John Patrick Amedori) ex-girlfriend, Lexi (guest star Natalie Knepp), expresses an interest in Dan (Penn Badgley) which creates conflicted feelings for Serena (Blake Lively). Nate (Chace Crawford), Jenny (Taylor Momsen) and Vanessa (Jessica Szohr) get into a tangled situation that puts their friendships and hearts on the line. Kelly Rutherford and Matthew Settle also star. Patrick Norris directed the episode written by Robby Hull.
