Episode 1
Aired Sep 1, 2008
Summer, Kind of Wonderful
Serena and Nate pretend they are a couple to cover up Nate's relationship with a married woman and that Serena has been mourning her break-up with Dan.
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Episode 2
Aired Sep 8, 2008
Never Been Marcused
Blair is thrilled to be dating royalty, and plans on becoming a royal herself, but Chuck has other plans for her and her new love; Dan and Serena decide to keep their recent hook-ups a secret; Nate discovers the downside to having an affair.
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Episode 3
Aired Sep 15, 2008
The Dark Night
Serena and Dan are forced to deal with their problems when a city-wide blackout traps them in an elevator; Blair questions the lack of passion in her relationship with Marcus; Nate struggles with his feelings for Vanessa and Catherine.
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Episode 4
Aired Sep 22, 2008
The Ex-Files
When Serena notices Dan cozying up to Amanda, the new girl in school, Blair and her minions decide to befriend Amanda and sabotage her budding romance; Vanessa uncovers a scandalous secret about Catherine; Lily finds herself drawn to Rufus.
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Episode 5
Aired Sep 29, 2008
The Serena Also Rises
Blair decides to sabotage her mother's fashion show when she learns that Eleanor has given Serena and her new socialite friend front row seats; Dan begins hanging out with Chuck; Lily discovers that her husband has been keeping a secret.
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Episode 6
Aired Oct 13, 2008
New Haven Can Wait
After a fight with Blair, Serena ditches plans to visit Brown and accepts an invitation to visit Yale, the school Blair has always dreamed of attending; a group of Skull and Bones members kidnaps Chuck; Nate and a coed hook up.
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Episode 7
Aired Oct 20, 2008
Chuck in Real Life
Vanessa blackmails Blair into being a nicer person; Blair entices Chuck to seduce Vanessa; Lily and Bart throw a housewarming party; Dan and Jenny discover a secret.
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Episode 8
Aired Oct 27, 2008
Pret-a-Poor-J
Jenny makes friends with a model (Willa Holland) who encourages her to confront Eleanor Waldorf, who has been trying to "borrow" Jenny's designs; Serena meets an artist and realizes they have instant chemistry; Blair tries to seduce Chuck.
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Episode 9
Aired Nov 3, 2008
There Might Be Blood
Serena discovers that Aaron has been keeping a secret from her; hoping it will help her get into Yale, Blair agrees to baby-sit the daughter of a prominent donor; Jenny and Agnes (Willa Holland) plan a guerrilla fashion show.
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Episode 10
Aired Nov 10, 2008
Bonfire of the Vanity
Blair despises Eleanor Waldorf's new boyfriend (Wallace Shawn) at first sight; Jenny moves in with Agnes as they move forward with their plans for a fashion line; Dan tries to win the trust of Bart Bass.
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Episode 11
Aired Nov 17, 2008
The Magnificent Archibalds
Blair is upset when her mother's boyfriend decides to ruin all of her favorite Thanksgiving traditions; Lily tries to broker a peace treaty between Rufus and Jenny; Eric uncovers a secret that Bart has been keeping from Lily.
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Episode 12
Aired Dec 1, 2008
It's a Wonderful Lie
Blair and Chuck make a bet that they can find the perfect dates for each other for the annual Snowflake Ball; Aaron's ex-girlfriend expresses interest in Dan, creating conflicting feelings for Serena.
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Episode 13
Aired Dec 8, 2008
O Brother, Where Bart Thou?
Tragedy strikes the lives of the Upper East Side teens and their parents.
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Episode 14
Aired Jan 5, 2009
In the Realm of the Basses
Uncle Jack Bass (Desmond Harrington) arrives in town to try and help Chuck pick up the pieces; Blair tries to get accepted into Colony Club, the most prestigious ladies club in the city; Jenny returns to Constance Billard.
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Episode 15
Aired Jan 12, 2009
Gone With the Will
Lily, Bart's brother, Jack, and Chuck learn the fate of the Bass empire; Rufus searches for details about the child he never knew he had; Dan uncovers Rufus and Lily's secret.
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Episode 16
Aired Jan 19, 2009
You've Got Yale!
Constance Billard and St. Jude's students find out who is worthy of early admission to Yale University; Serena bonds with a new teacher (Laura Breckenridge); Chuck teams up with an unlikely ally in his war against Jack.
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Episode 17
Aired Feb 2, 2009
Carnal Knowledge
Blair devises a plan to bring down a teacher; Chuck wakes up in a hotel with little memory of what happened the previous evening.
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Episode 18
Aired Mar 16, 2009
The Age of Dissonance
Serena develops a crush on the director of the school play; Blair gets devastating news about her future; Dan and Rachel have a hard time staying away from each other.
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Episode 19
Aired Mar 23, 2009
The Grandfather
Devastated by recent events, Blair explores her dark side; Lily and Rufus decide to be completely honest with each other.
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Episode 20
Aired Mar 30, 2009
Remains of the J
Serena decides to plan a small party for Jenny's 16th birthday; Vanessa helps Chuck with a scheme involving Nate and Blair; Rufus discovers that Dan won't receive financial aid from Yale.
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Episode 21
Aired Apr 20, 2009
Seder Anything
Serena returns from her trip with Gabriel and Poppy; Blair and Nate's grandfather make a deal; Dan tries to earn money for college.
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Episode 22
Aired Apr 27, 2009
Southern Gentlemen Prefer Blondes
Georgina Sparks returns after undergoing a transformation; Nate and Chuck come to a crossroads in their relationship; Serena's relationship with Gabriel gets more complicated.
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Episode 23
Aired May 4, 2009
The Wrath of Con
Blair pressures Georgina into helping her with a scheme; Chuck and Nate's rivalry comes to a head; Lily comes up with a secret plan.
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Episode 24
Aired May 11, 2009
Valley Girls
Lily remembers getting kicked out of boarding school when she was 17; Nate and Blair's evening at the prom does not go as planned; Lily and Serena clash.
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Episode 25
Aired May 18, 2009
The Goodbye Gossip Girl
Gossip Girl shakes things up by sending out a damaging e-mail blast during the commencement ceremony; Rufus and Lily try to repair their relationship.
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