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From invisible outsider to the boyfriend of Serena, the most beautiful and sought-after socialite in New York, Dan Humphrey is at least partly responsible for making Brooklyn the new Manhattan, right?Along the way he romanced Vanessa, Georgina, Olivia, got weirdly close with Blair, interned at Now: Penn Badgley certainly has shades of Dan in him: He was also too smart for high school (he started college at 14).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.

Around season four, he peaced out to Sarah Lawrence College and only returned for a brief good-bye in the finale (like Jenny).

Hilary Duff came to the Upper East Side as a famous actress who hid her identity from Dan (and being Dan, it takes him eons to figure it out — yet he managed to fool everyone around him for years. Now: The jump to Then: Finally, the female Chuck Bass.

Raina came into the picture as Chuck's business adversary, and all that tension quickly led to a not-so-hostile takeover (wink, wink).

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.

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Pick your model poison really, because she embodied all the "bad girl" behavior we associate with PYTs.

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