The series begins with the return of Serena van der Woodsen (Blake Lively) from a mysterious stay at a boarding school in Connecticut. Blair Waldorf (Leighton Meester), who creators describe as the queen at the center of their chess game, is a longtime friend and occasional rival of Serenas, and the Queen Bee of Constance Billard Schools social scene. The story also follows Chuck Bass (Ed Westwick), the bad boy of the Upper East Side, Nate Archibald (Chace Crawford), Chucks best friend, and other characters of the turbulent Manhattan scene: Dan Humphrey (Penn Badgley), Nates friend and Serenas onagain, offagain ex; Vanessa Abrams (Jessica Szohr), Dans best friend; and Dans ambitious sister Jenny Humphrey (Taylor Momsen)