10. Queen B Dethroned
As Blair (Leighton Meester) deals with a nasty pregnancy rumor, her clique gives her the cold shoulder upon learning that she cheated on her boyfriend Nate (Chace Crawford) with his best friend Chuck (Ed Westwick).
Gossip Girl’s Top 10 OMG Moments!
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9. Return of Mr. van der Woodsen
After Serena (Blake Lively) combed through Europe searching for her father (William Baldwin), he resurfaces to treat her mother's cancer. One catch? He's more interested in rekindling things with his ex-wife, who's currently married to Rufus (Matthew Settle).
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8. Jenny Dates a Drug Dealer
Careful, Little J! When Jenny (Taylor Momsen) begins dating drug-dealer Damien (Kevin Zegers) behind her father's back, the troubled teen soon begins peddling drugs herself.
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7. Chuck and Blair's Limo Lust
After Blair seduces Chuck with a sexy striptease at the burlesque nightclub Victrola, the two -- finally! -- hook up in a limo on their way home.
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6. College Catfight
Hell hath no fury like a frenemy scorned! When Yale University courts Serena, Blair thinks her BFF is stealing her dream. Her response? A full-on girl fight at a university-sponsored party, shocking the Yale administration.
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5. Three's a Crowd
Fearing they're missing out on the college experience, Olivia (Hilary Duff) hatches a plan with Dan (Penn Badgley) and Vanessa (Jessica Szohr) to have a threesome. One problem: after the deed is done, Dan develops feelings for Vanessa, creating a messy love triangle.
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4. Murder Mystery
When Georgina (Michelle Trachtenberg) returns to the Upper East Side and begins to torment Serena, Blair confronts her nervous BFF -- and got the most shocking news of Season 2. "I killed someone," Serena reveals coldly.
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3. Lil J Jumps Into Bed With Chuck
A vulnerable and misguided Jenny calls losing her virginity to Chuck (who tried to rape her three years ago) "a mistake" after her supposed paramour does the deed and runs back to Blair in season three.
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2. Gossiping For Two
Baby on board! Trachtenberg's Georgina Sparks returned to the CW series in a big way -- announcing on the third season finale she is pregnant -- with Dan's baby.
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1. Bullet Wounds
Could a single shot silence Chuck Bass for good? In the final moments of season three's finale, Chuck was cornered in an alley as thieves attempted to steal the engagement sparkler he'd intended to give Blair -- that is, until she found out he slept with Jenny!
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