Episode 1 – Summer, Kind Of Wonderful – Original Air Date – 09/01/2008
TV Ratings : 3.38 Million Viewers | Adults 18-49: 1.7/5
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GOSSIP GIRL INVADES THE HAMPTONS / GUEST STARS INCLUDE AUTHOR JAY MCINERNEY, SOCIALITE TINSLEY MORTIMER AND ACTRESS MADCHEN AMICK — 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 (#201).
Episode 2 – Never Been Marcused – Original Air Date – 09/08/2008
TV Ratings : 3.16 Million Viewers | Adults 18-49: 1.6/4
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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 hew 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 (#202).
Episode 3 – The Dark Night – Original Air Date – 09/15/2008
Promo Photos For 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 (#203).
Episode 4 – The Ex Files – Original Air Date – 09/22/2008
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 (#204).
Episode 5 – The Serena Also Rises – Original Air Date – 09/29/2008
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 (#205).
Episode 6 – New Haven Can Wait – Original Air Date – 10/13/2008
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 (#206).
Episode 7 – Chuck In Real Life – Original Air Date – 10/20/2008
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 (#207).
Episode 8 – Pret-a-Poor-J – Original Air Date – 10/27/2008
WILLA HOLLAND (“THE O.C.”) GUEST STARS AND A NEW LOVE INTEREST FOR SERENA (JOHN PATRICK AMEDORI) IS INTRODUCED — 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 (#208).
Episode 9 – There Might Be Blood – Original Air Date – 11/03/2008
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 (#209).
Episode 10 – Bonfire Of The Vanity – Original Air Date – 11/10/2008
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 (#210).
Episode 11 – The Magnificent Archibalds – Original Air Date – 11/17/2008
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 (#211).
Episode 12 – It’s A Wonderful Lie – Original Air Date – 12/01/2008
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 (#212).
Episode 13 – O Brother, Where Bart Thou? – Original Air Date – 12/08/2008
TRAGEDY STRIKES — A sudden and tragic event impacts the lives of our favorite Upper East Side teens and their parents. Blake Lively, Leighton Meester, Penn Badgley, Chace Crawford, Taylor Momsen, Ed Westwick, Kelly Rutherford and Matthew Settle star. Joe Lazarov directed the episode written by Stephanie Savage (#213).
Episode 14 – In The Realm Of The Basses – Original Air Date – 1/5/2009
UNCLE JACK BASS (GUEST STAR DESMOND HARRINGTON, “DEXTER”) ARRIVES ON THE SCENE — With Chuck (Ed Westwick) MIA since his father’s funeral, Uncle Jack (Harrington) arrives on the Upper East Side to help Chuck pick up the messy pieces, but first he has to find him. Trying her best to forget her last painful exchange with Chuck, Blair (Leighton Meester) focuses her attention on being accepted into the most prestigious ladies club in the city, Colony Club. Jenny (Taylor Momsen) returns to Constance Billard and immediately takes on Penelope (guest star Amanda Setton) and her posse of mean girls, but no one is going down without a valiant Gossip Girl-worthy fight. Blake Lively, Penn Badgley, Kelly Rutherford and Matthew Settle also star. Tony Wharmby directed the episode written by John Stephens (#214).
Episode 15 – Gone With The Will – Original Air Date – 1/12/2009
THE READING OF BART BASS’ WILL — With the reading of Bart’s will, Chuck (Ed Westwick), Bart’s brother, Jack (guest star Desmond Harrington), and Lily (Kelly Rutherford) learn the fate of the Bass empire. Rufus (Matthew Settle) and Lily’s relationship is strained as Rufus seeks details about the child he never knew he had. Noticing that his father has been acting strangely as of late, Dan (Penn Badgley) does some investigating and uncovers Rufus and Lily’s secret, putting him in the awkward situation of deciding what to do with this shocking revelation and who to share it with. Blake Lively, Leighton Meester, Chace Crawford, Taylor Momsen and Jessica Szohr also star. Tricia Brock directed the episode written by Amanda Lasher (#215).
Episode 16 – You’ve Got Yale – Original Air Date – 1/19/2009
WHICH OF OUR FAVORITE UPPER EAST SIDERS ARE GOING TO BE ATTENDING YALE IN THE FALL? — It’s that stressful time of year when Constance Billard and St. Jude’s students find out who is and isn’t worthy of early admission to Yale University. Serena (Blake Lively) bonds with her new Shakespeare teacher, Rachel (guest star Laura Breckenridge), who has no clue the wrath she is about to suffer after giving Blair (Leighton Meester) the first B of her prep school career. Chuck (Ed Westwick) pairs up with an unlikely ally in his war with Jack (guest star Desmond Harrington) over Bass Industries. Nate (Chace Crawford) and Vanessa (Jessica Szohr) spend a romantic evening at the opera. Taylor Momsen, Kelly Rutherford and Matthew Settle also star. Janice Cooke directed the episode written by Joshua Safran (#216).
Episode 17 – Carnal Knowledge – Original Air Date – 2/2/2009
BLAIR IS IN THE MOOD FOR A LITTLE REVENGE — In retaliation for not playing by the unspoken rules of Constance Billard, Blair (Leighton Meester) hatches a plan to bring down her teacher, Rachel (guest star Laura Breckenridge), and it’s going to be good. After Chuck (Ed Westwick) wakes up in a hotel and only has a minor recollection of what happened the previous evening and who he spent the evening with, Nate (Chace Crawford) and Vanessa (Jessica Szohr) try to help him fill in the missing pieces of what is turning out to be an increasingly intriguing mystery. Blake Lively, Penn Badgley, Taylor Momsen, Kelly Rutherford and Matthew Settle also star. Liz Allen directed the episode written by Alexandra McNally & Lenn K. Rosenfeld (#217).
Episode 18 – The Age Of Dissonance – Original Air Date – 3/16/2009
THE SENIORS PUT ON A PRODUCTION OF “THE AGE OF INNOCENCE”/SEBASTIAN STAN (“KINGS”) RETURNS AS CARTER BAIZEN — The Constance Billard and St. Jude seniors put on a production of “The Age of Innocence” and find their personal lives mirroring conflicts in the play. Serena (Blake Lively) develops a crush on the play’s director, Julian (guest star Harmon Walsh), and enlists Vanessa’s (Jessica Szohr) knowledge of theater to help her get the otherwise uninterested guy’s attention. Blair (Leighton Meester) receives devastating news about her future that leads her on a witch-hunt for the person responsible. Dan (Penn Badgley) and Rachel (guest star Laura Breckenridge) agree to stay away from each other in the aftermath of being discovered as more than teacher and student, but find it impossible to keep that promise. Chuck (Ed Westwick) enlists help from an unlikely source, his nemesis Carter Baizen (guest star Sebastian Stan). Chace Crawford, Taylor Momsen and Matthew Settle also star. Norman Buckley directed the episode written by Jessica Queller (#218).
Episode 19 – The Grandfather – Original Air Date – 3/23/2009
BLAIR WALDORF EXPLORES HER DARK SIDE — Devastated by the recent plot twist in her life, Blair (Leighton Meester) turns her back on her predictable Waldorf existence in favor of a more wild and unpredictable lifestyle, causing Serena (Blake Lively) and Chuck (Ed Westwick) to have serious concerns about their friend. Vanessa (Jessica Szohr) convinces Nate (Chace Crawford) that it may be time to forgive and forget when it comes to his mother’s Kennedyesque family, The Vanderbilts, who abandoned Nate and his mother when they needed them most. In a misguided effort to be completely honest with each other, Lily (Kelly Rutherford) and Rufus (Matthew Settle) agree to share lists of their past lovers. Penn Badgley and Taylor Momsen also star. J. Miller Tobin directed the episode written by Robby Hull & Etan Frankel (#219).
Episode 20 – Remains Of The J – Original Air Date – 3/30/2009
JENNY’S KINDA-NOT-SWEET SIXTEEN / TAMARA FELDMAN & ARMIE HAMMER GUEST STAR — Serena (Blake Lively) decides to throw Jenny (Taylor Momsen) an intimate party for her sixteenth birthday, but things get way out of control when Poppy Lifton (guest star Tamara Feldman) turns the small gathering into a huge social event. In a moment of weakness, Vanessa (Jessica Szohr) agrees to help Chuck (Ed Westwick) with a scheme having to do with Blair (Leighton Meester) and Nate (Chace Crawford). Rufus (Matthew Settle) learns that Dan (Penn Badgley) will not receive financial aid at Yale and tries to figure out another way to cover the cost of his education. Kelly Rutherford also stars. Armie Hammer guest stars as Poppy’s boyfriend, Gabriel. Allison Liddi-Brown directed the episode written by Sarah Frank-Meltzer (#220).
Episode 21 – Seder Anything – Original Air Date – 4/20/2009
SERENA RETURNS FROM SPAIN — Serena (Blake Lively) returns from her trip to Spain with Poppy (guest star Tamara Feldman) and Gabriel (guest star Armie Hammer). Blair (Leighton Meester) makes a secret deal with Nate’s (Chace Crawford) grandfather, William (guest star James Naughton), and Nate learns some disturbing information about his father’s arrest. Dan (Penn Badgley) takes a job as a cater-waiter to earn money for college, but is distressed when he discovers the gig is a Passover seder at the Waldorf penthouse and several of his friends and family are guests. Taylor Momsen, Ed Westwick, Kelly Rutherford and Matthew Settle also star. John Stephens directed the episode written by Amanda Lasher (#221).
Episode 22 – Southern Gentlemen Prefer Blondes – Original Air Date – 4/27/2009
GEORGINA IS BACK! — Georgina (guest star Michelle Trachtenberg, “17 Again”) returns to the Upper East Side after undergoing a major transformation. Chuck (Ed Westwick) and Nate (Chace Crawford) find themselves at a major crossroads in their relationship as it pertains to their mutual interest in Blair (Leighton Meester). Serena (Blake Lively) finds her relationship with Gabriel (guest star Armie Hammer) growing more complicated. Penn Badgley, Taylor Momsen, Jessica Szohr, Kelly Rutherford and Matthew Settle also star. Patrick Norris directed the episode written by Leila Gerstein
Episode 23 – The Wrath Of Con – Original Air Date – 5/04/2009
NATE VS. CHUCK / MICHELLE TRACHTENBERG GUEST STARS — Blair (Leighton Meester) pressures Georgina (Trachtenberg) into making amends for her past bad behavior by helping her in a scheme. The rivalry between Nate (Chace Crawford) and Chuck (Ed Westwick) over Blair comes to a head. Lily (Kelly Rutherford) hatches a secret plan to help Rufus (Matthew Settle) with Dan’s (Penn Badgley) college tuition. Blake Lively, Taylor Momsen and Jessica Szohr also star. Janice Cooke Leonard directed the episode written by Sara Goodman (#223).
Episode 24 – Valley Girls – Original Air Date – 5/11/2009
EPISODE FEATURES GUEST STARS BRITTANY SNOW (“AMERICAN DREAMS”), KRYSTEN RITTER (“CONFESSIONS OF A SHOPAHOLIC”), 80S ICON ANDREW MCCARTHY, MICHELLE TRACHTENBERG (“17 AGAIN”) AND A PERFORMANCE BY NO DOUBT — In a flashback to the 80s, 17-year-old Lily Rhodes (Snow) gets kicked out of boarding school and runs away to Los Angeles, reconnecting with her parents, Rick (McCarthy) and Cece (guest star Cynthia Watros, “Lost”), and sister, Carol (Ritter). Back in present day, Blair (Leighton Meester) and Nate (Chace Crawford) attend prom together, but the evening doesn’t turn out exactly as planned and Chuck (Ed Westwick) has a little something to do with that. Serena (Blake Lively) and Lily (Kelly Rutherford) don’t see eye-to-eye over Serena’s recent run-in with the law. No Doubt performs in the episode as an 80s band called “Snowed Out.” Penn Badgley, Taylor Momsen, Jessica Szohr and Matthew Settle also star. Marc Piznarski directed the episode written by Josh Schwartz & Stephanie Savage (#224).
Episode 25 – The Goodbye Gossip Girl – Original Air Date – 5/18/2009
GRADUATION, GOSSIP GIRL DRAMA AND CLIFFHANGERS GALORE! — Gossip Girl decides to liven things up at the Constance Billard and St. Jude’s graduation by sending out a shocking and damaging email blast in the midst of the commencement ceremony, stirring Serena (Blake Lively) to come up with a plan of attack. The Mean Girls (guest stars Yin Chang, Nicole Fiscella, Amanda Setton and Dreama Walker) challenge Jenny (Taylor Momsen) to throw her hat in the ring to succeed Blair (Leighton Meester) as Queen Bee next year. Lily (Kelly Rutherford) and Rufus (Matthew Settle) struggle to repair their relationship after Lily’s betrayal. As for the cliffhangers, Blair and Chuck (Ed Westwick) finally…and Serena is shocked by…and Georgina (guest star Michelle Trachtenberg) decides to…and Dan (Penn Badgley), Nate (Chace Crawford) and Vanessa (Jessica Szohr) unknowingly….and it all happens in the series’ climactic season finale. Norman Buckley directed the episode written by Joshua Saffran (#225).
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