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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).
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.
Once back in NY, she scores a job at Then: After a Paris meet-cute, Blair and Prince Louis went on a disastrous double date with Serena and his undercover security guard, with Blair throwing a tantrum when she thinks it's Serena who got the prince.
Well we know all their secrets, and we're totally here to tell.
After being outed by the maniacal Georgina, he had a few semi-serious relationships before getting mixed up with drugs and the duplicitous, Serena-obsessed Damian.
Around season four, he peaced out to Sarah Lawrence College and only returned for a brief good-bye in the finale (like Jenny).
(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).
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.
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).