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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?

Around season four, he peaced out to Sarah Lawrence College and only returned for a brief good-bye in the finale (like Jenny).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.Maybe Carter settled into life in the desert and sells T-shirts at Coachella now.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).

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