The Best Episodes of Gossip Girl Season 2

#1 Fan Favorite
8.5/10(1361 votes)
#1 - The Goodbye Gossip Girl
S2:E255/18/2009
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 to come up with a plan of attack. The Mean Girls challenge Jenny to throw her hat in the ring to succeed Blair as Queen Bee next year. Lily and Rufus struggle to repair their relationship after Lily's betrayal. As for the cliffhangers, Blair and Chuck finally... and Serena is shocked by... and Georgina decides to... and Dan, Nate, and Vanessa unknowingly.... Jenny and Eric do something they might end up regretting.
Director:Norman Buckley
Writer:Joshua Safran
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Director:Norman Buckley
Writer:Joshua Safran
8.4/10(1247 votes)
#2 - O Brother, Where Bart Thou?
S2:E1312/8/2008
The entire Upper East Side of Manhattan is rocked when Bart Bass dies suddenly in a limo accident. Serena and Eric take the news very calmly while Lily has a troubling time despite her mother, Cece's, awkward attempts to comfort her. Chuck begins to blame Lily for his father's death and threatens to reveal a secret that Bart found on her before his accident. Meanwhile, Blair's mother, Eleanor, prepares for her latest marriage to Aaron's father Cyrus.
Director:Joe Lazarov
Writer:Stephanie Savage
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Director:Joe Lazarov
Writer:Stephanie Savage
8.0/10(1117 votes)
#3 - Pret-a-Poor J
S2:E810/27/2008
Jenny has a new young model friend, named Agnes, who encourages Jenny to explore her wild side, and also to confront Eleanor Waldorf who is planning to steal Jenny's designs in order to pass them off as her own. Meanwhile, Serena and Dan attend Rufus' latest art opening as friends, but then Serena meets an artist, named Aaron Rose, and the evening gets a little uncomfortable for Dan. Elsewhere, Blair attempts to seduce Chuck, but he proves to be tougher than she ever imagined. Also, Jenny begins to have a mutual feelings with Nate as he's staying with her, Dan, and Rufus while searching for a place to live.
Director:Vondie Curtis-Hall
Writer:Amanda Lasher
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Director:Vondie Curtis-Hall
Writer:Amanda Lasher
8.0/10(1195 votes)
#4 - Valley Girls
S2:E245/11/2009
In a flashback to the 80s, 17-year-old Lily Rhodes gets kicked out of boarding school and runs away to Los Angeles, reconnecting with her parents, Rick and Cece, and sister, Carol. Back in present day, Blair and Nate attend prom together, but the evening doesn't turn out exactly as planned and Chuck and Serena have a little something to do with that. Serena and Lily don't see eye-to-eye over Serena's recent run-in with the law.
Director:Mark Piznarski
Writers:Stephanie Savage, Josh Schwartz
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Director:Mark Piznarski
Writers:Stephanie Savage, Josh Schwartz
7.9/10(1410 votes)
#5 - Summer Kind of Wonderful
S2:E19/1/2008
As the summer draws to a close in the Hamptons, Serena and Nate 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. Blair returns from abroad with a hot guy on her arm, making a very jealous Chuck question his decision to leave Blair stranded at the heliport. Dan has spent the summer assisting a famous author. While interning for Eleanor Waldorf's company, Jenny sneaks an invite to a much-coveted Hamptons' White Party at which Eric introduces her to socialite Tinsley Mortimer.
Director:J. Miller Tobin
Writer:Joshua Safran
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Director:J. Miller Tobin
Writer:Joshua Safran
7.9/10(1038 votes)
#6 - There Might be Blood
S2:E911/3/2008
Serena invites Aaron to a charity event, but soon uncovers a secret Aaron has been keeping from her. Thinking it will help her get into Yale, Blair agrees to babysit the 15-year-old daughter of a Yale donor, but her plan quickly backfires. Meanwhile, Jenny and Agnes plan a fashion show.
Director:Michael Fields
Writers:Etan Frankel, John Stephens
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Director:Michael Fields
Writers:Etan Frankel, John Stephens

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The 20 BEST Episodes of Gossip Girl

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7.9/10(953 votes)
#7 - The Wrath of Con
S2:E235/4/2009
Blair puts pressure on Georgina to making amends for her past bad behavior by helping her in an evil plan. The rivalry between Nate and Chuck over Blair reaches a boiling point. Lily makes a secret plan to help Rufus with Dan's college tuition.
Director:Janice Cooke
Writer:Sara Goodman
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Director:Janice Cooke
Writer:Sara Goodman
7.8/10(1066 votes)
#8 - The Serena Also Rises
S2:E59/29/2008
In the midst of Fashion Week, a furious Blair learns that her mother, Eleanor, at the suggestion of her protege Jenny, has given Serena and her new socialite friend, Poppy Lifton, 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 starts hanging out with Chuck, but a walk on the dark side always has its risks and Dan learns that the hard way. Lily learns a secret that her new husband, Bart, has been keeping from her.
Director:Patrick R. Norris
Writer:Jessica Queller
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Director:Patrick R. Norris
Writer:Jessica Queller
7.8/10(1065 votes)
#9 - Chuck in Real Life
S2:E710/20/2008
Vanessa uses the scandalous picture of Catherine and Marcus to blackmail Blair into being a nicer person, so Blair seeks revenge by enticing Chuck to seduce Vanessa. Lily and Bart throw an extravagant housewarming party and expect their children to make them proud in front of the attending press, but a rebellious Serena isn't ready to play by their rules. Meanwhile, Dan and Jenny discover a big secret that Nate has been keeping from his friends.
Director:Tony Wharmby
Writer:Lenn K. Rosenfeld
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Director:Tony Wharmby
Writer:Lenn K. Rosenfeld
7.8/10(1000 votes)
#10 - In the Realm of the Basses
S2:E141/5/2009
Because Chuck is MIA since his father's funeral, his Uncle Jack arrives on the Upper East Side to find and help him. Trying to forget her last conversation with Chuck, Blair focuses on being accepted into the most prestigious ladies club in the city, Colony Club. Jenny returns to Constance Billard and immediately takes on Penelope and her posse of mean girls, but no one is going down without a valiant Gossip Girl-worthy fight.
Director:Tony Wharmby
Writer:John Stephens
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Director:Tony Wharmby
Writer:John Stephens
7.8/10(968 votes)
#11 - Gone with the Will
S2:E151/12/2009
Chuck, Jack and Lily come together for the reading of the will which reveals what will come of the Bass empire. Rufus and Lily's relationship is put on hold as Rufus searches for the child he never knew he had. Meanwhile, Dan does some digging of his own and uncovers Rufus and Lily's secret, putting him in an awkward position.
Director:Tricia Brock
Writer:Amanda Lasher
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Director:Tricia Brock
Writer:Amanda Lasher
7.7/10(1040 votes)
#12 - New Haven Can Wait
S2:E610/13/2008
After Blair and Serena 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 frantically tries to figure out a way to salvage his chances of getting into the school. While on the Yale campus, Chuck is kidnapped by a group of Skull and Bones members and Nate hooks up with a co-ed.
Director:Norman Buckley
Writers:Joshua Safran, Alexandra McNally
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Director:Norman Buckley
Writers:Joshua Safran, Alexandra McNally
7.7/10(955 votes)
#13 - The Magnificent Archibalds
S2:E1111/17/2008
It's Thanksgiving time and Blair is offended when her Mom's new man hijacks her Thanksgiving traditions. Lily attempts to strengthen the frail bond between Rufus and Jenny. Eric discovers a secret about Bart. Vanessa and Chuck help Nate deal with his father.
Director:Jean de Segonzac
Writer:Joshua Safran
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Director:Jean de Segonzac
Writer:Joshua Safran
7.7/10(993 votes)
#14 - It's a Wonderful Lie
S2:E1212/1/2008
At the Snowflake dance, Blair and Chuck discover their lookalikes hooking up. Aaron's ex Lexi flirts with Dan, causing trouble with Serena. Nate, Jenny and Vanessa get into a messy love triangle that involves a stolen letter and a revealing dress. Bart Bass suffers a car accident on his way to the ball.
Director:Patrick R. Norris
Writer:Robby Hull
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Director:Patrick R. Norris
Writer:Robby Hull
7.7/10(993 votes)
#15 - You've Got Yale
S2:E161/19/2009
The students are stressed out as they find out who was accepted and who didn't make the cut for early admission to Yale. Meanwhile, Serena bonds with Rachel, her Shakespeare teacher, who is unaware of what Blair has in store for her following receiving her first B; Chuck finds an unlikely ally in his feud with Jack; and Nate and Vanessa have a romantic evening together.
Director:Janice Cooke
Writer:Joshua Safran
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Director:Janice Cooke
Writer:Joshua Safran
7.6/10(1079 votes)
#16 - The Dark Night
S2:E39/15/2008
In a humorous twist, Blair questions the lack of passion in her relationship with Marcus, while at the same time Chuck appears to have lost his "passion" for any woman other than Blair. Meanwhile, Nate struggles between his feelings for Vanessa and his more-complicated-by-the-day relationship with Catherine. Jenny risks losing her internship when Eleanor catches Jenny critiquing one of the Eleanor Waldorf designs.
Director:Janice Cooke
Writer:John Stephens
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Director:Janice Cooke
Writer:John Stephens
7.6/10(1053 votes)
#17 - The Ex-Files
S2:E49/22/2008
Blair and her minions decide to befriend the new girl, Amanda, in order to sabotage her possible new relationship with Dan. Vanessa discovers a scandalous secret about Catherine and enlists Blair's scheming expertise to use the information to help Nate. Meanwhile, Lily finds herself drawn back to her ex, Rufus, once again.
Director:Jim McKay
Writer:Robert Hull
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Director:Jim McKay
Writer:Robert Hull
7.6/10(986 votes)
#18 - Carrnal Knowledge
S2:E172/2/2009
Blair comes up with a devious plan to take down her new teacher, Rachel. Chuck has no recollection of what happened to him when he wakes up in a hotel. Nate and Vanessa try to help Chuck fill in the missing pieces of his night. Meanwhile Dan and Serena try to keep their relationship together as Rufus and Lily grow even closer.
Director:Elizabeth Allen Rosenbaum
Writers:Lenn K. Rosenfeld, Alexandra McNally
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Director:Elizabeth Allen Rosenbaum
Writers:Lenn K. Rosenfeld, Alexandra McNally
7.6/10(919 votes)
#19 - Seder Anything
S2:E214/20/2009
Serena returns from her trip to Spain with Poppy and Gabriel. Blair makes a secret deal with Nate's grandfather. Dan takes a job to earn money for college.
Director:John Stephens
Writer:Amanda Lasher
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Director:John Stephens
Writer:Amanda Lasher
7.6/10(888 votes)
#20 - Southern Gentlemen Prefer Blondes
S2:E224/27/2009
Georgina returns to the Upper East Side but it's not the same Georgina we all knew, she's changed. Chuck and Nate's relationship is at a crossroads because of their mutual interest in Blair. Serena's relationship with Gabriel gets more complicated.
Director:Patrick R. Norris
Writer:Leila Gerstein
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Director:Patrick R. Norris
Writer:Leila Gerstein
7.5/10(1078 votes)
#21 - Never Been Marcused
S2:E29/8/2008
Blair is over the moon that she is dating royalty and has every intention of becoming a royal herself, but a scheming Chuck has other plans for Blair and her new love, Marcus, when he introduces Blair to Marcus' stepmother who happens to be Catherine. Meanwhile, Nate learns the downside to having an affair with Catherine when he keeps getting caught in his lies and learns his family has gone bankrupt due to his father jumping bail.
Director:Michael Fields
Writer:Stephanie Savage
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Director:Michael Fields
Writer:Stephanie Savage
7.5/10(965 votes)
#22 - Bonfire of the Vanity
S2:E1011/10/2008
Blair sets out on a mission to break up her mother and Cyrus Rose, her new man. Jenny moves in with Agnes as the two continue with their plans for their own fashion line. As Serena continues to fall for Aaron, she learns something that may derail their relationship forever while Dan interviews Bart Bass for an article for New York Magazine.
Director:David Von Ancken
Writer:Jessica Queller
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Director:David Von Ancken
Writer:Jessica Queller
7.4/10(965 votes)
#23 - The Age of Dissonance
S2:E183/16/2009
The Constance Billard and St. Jude seniors have the production of "The Age of Innocence". Serena has a crush on the play's director, Julian, and enlists Vanessa's knowledge of theater to help her get the guy's attention. Blair receives bad news about her future that leads her on a witch hunt for the person responsible. Dan and Rachel 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 find help on an unlikely friend, Carter Baizen.
Director:Norman Buckley
Writer:Jessica Queller
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Director:Norman Buckley
Writer:Jessica Queller
7.3/10(913 votes)
#24 - The Grandfather
S2:E193/23/2009
Devastated by the turn her life has taken, Blair opts for a wild lifestyle instead of her perfect Waldorf life, causing Chuck and Serena to become concerned. Vanessa tries to convince Nate that he needs to move on after his mother's family, the Vanderbilts, abandoned him and his mother. Trying to be honest with each other, Lily and Rufus both put together their lists of past relationships.
Director:J. Miller Tobin
Writers:Etan Frankel, Robby Hull
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Director:J. Miller Tobin
Writers:Etan Frankel, Robby Hull
7.3/10(897 votes)
#25 - Remains of the J
S2:E203/30/2009
Serena throws Jenny a sixteenth birthday party, but things spin out of control when Poppy Lifton turns the party into the social event of the season. Vanessa agrees to help Chuck in a plan concerning Blair and Nate. Meanwhile, Rufus searches for a way to cover Dan's tuition when he learns he will not receive financial aid to go to Yale.
Director:Allison Liddi-Brown
Writer:Sarah Frank-Meltzer
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Director:Allison Liddi-Brown
Writer:Sarah Frank-Meltzer