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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.She is ultimately responsible for having Dan's book published, and the last we saw of her, she's working on set for that bunk Then: Feel free to disagree with this, but Carter, Chuck's smarmy nemesis, was slightly (very) hot, in a "sleep with him but never admit it to your friends" kind of way.Carter functioned like Chuck and Nate's gateway drug — he was the first to give them pot and sneak them into nightclubs.preferring to focus her attention on her band, The Pretty Reckless.Her character went on "indefinite hiatus" during the show's fourth season (as noted above), but did return for the grand finale.After an ill-fated pregnancy, Blair and Chuck's ongoing love/hate relationship and the Prince's cold-as-ice post-ceremony confession — that he's only in it for the optics — the two quickly divorce, because not even the Grimaldis can stand in the way of the Bass. finds Chuck wounded on the street after a botched robbery and nurses him back to health, eventually taking him to Paris and then convincing him to return home to New York (where he even tries to shake his playboy identity with a new philanthropic persona).

Nate broke Blair's heart, and then had his heart broken by Serena, while Chuck bedded every model and wannabe socialite above 60 Then: Brooklyn rebel Jenny Humphrey never quite fit in with the UES crowd — but that didn't stop her from climbing all the way to the top of those Met steps.Now: Michelle Trachtenberg had the perfect inspo for Georgina — her own teenage years at a prestigious but vicious private school.While she's still best known for her turns on Then: Serena's sensitive, smart and occasionally institutionalized brother is both a player and a pawn in the (mind)games Serena, Chuck, Dan, Blair and Jenny excel at.She went from an impressionable minion to the Queen Bee of Constance, but it wasn't built to last; after GG reveals that Jenny slept with Chuck, she's slut-shamed and banished to somewhere upstate (past the Bronx, even, we think).Jenny most encapsulated the crushing humiliation, joy and, well, more crushing humiliation of being a teenager, finally harnessing her ambition and talent into a clothing line (which is much cooler than a headband).Much like Georgina, when Carter popped up, you knew trouble was close by; he also at some point became indebted to the Buckley family and had to work off his debt on an oil rig. ) The last we see of Carter is when he's caught lying to Serena — she retaliates by kicking him out of her limo, which is en route to Palm Springs in search of her dad.

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