Blair Waldorf (full name: Blair Cornelia Waldorf ) is an Upper East Sider, and then some. She is the daughter of Harold Waldorf, Esq., and high-end fashion designer Eleanor Waldorf. (In Season 1, her father leaves her mother for a French male model, and runs off to Paris.) A hopeless romantic who idolizes Audrey Hepburn, Blair has a sensitive side that contrasts with her tendency to be bitchy and controlling. Her predatory nature combined with her social clout, money, and beguiling charm get her whatever she wants—and it’s definitely more fun when Blair gets what she wants. Wealthy and snobby, yet good-natured, Blair is known for her “Queen B” status at the exclusive Constance Billard School. Although Blair seems self-confident and vain, her close friendship with It Girl Serena van der Woodsen causes her to be insecure at times. Blair’s tumultuous love life begins with her rollercoaster relationship with Nate Archibald—and just keeps rolling. In Season 1, she loses her virginity to Nate’s on-again, off-again BFF Chuck Bass (also her close friend and plotting ally) in the back of Chuck’s father’s limo (OMFG!). A good portion of Blair's storyline in Season 2 revolves around her love/hate relationship with Chuck. Fashion footnote: Blair Waldorf has brought back the headband, full force.