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But psych, that's just the first of her many schemes, from bedding Dan to finding Jesus to faking her baby's paternity.
She had a love/hate relationship with the GG inner circle, and her one-liners and stomach for ruthlessness were some of the show's best "OMG, is this bitch for real?! She ended her reign of terror after finally meeting her match, Chuck's skeevy uncle Jack.
Now: Connor, who attended acting school with Taylor Momsen and Then: Brooklyn's resident hip wet blanket, Vanessa mainly functioned as the "angel voice" on Dan's shoulder, but still juggled on-and-off relationships with him and Nate.
Mostly, though, she wore statement necklaces and got involved in schemes that were way above her pay grade.
(Incidentally, among other projects, Blake Lively had two kids and starred in a shark movie and Leighton Meester appeared alongside Then: Blair and Serena were no doubt the Upper East Side's main attraction, but poor little rich boys Nate and Chuck made for fun sideshows (and, at times, sidepieces).