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).
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).
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.
Not all is lost when Louis shows up in New York — with one of Blair's shoes — and the two resume their romance, becoming engaged despite the royal family's deep dislike of Blair.
Hey, Upper East Siders, ever wonder what happened to the scheming socialites and Gatsby-esque villains who seemed to always circle S and B?
Well we know all their secrets, and we're totally here to tell.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.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).Eventually, though, Eva was driven out of town by Waldorf's incessant meddling and manipulation. Now: Clémence is an accomplished actress and model, appearing in the Then: What better way to transition out of Disney handcuffs than with a girl-on-girl turn on The CW Network? Oh, and before she left school and town forever, they offer her the true college experience, which obviously includes shots and a threesome.Then: Nelly Yuki is a lesson for the kids: Do not peak in high school!