Serena van der Woodsen (Blake Lively) on Gossip Girl
Back in Season 1 Gossip Girl, lovebirds Blair (Leighton Meester) and Nate (Chace Crawford) were without a doubt the Upper East Side’s reigning power couple. Too bad Nate had to go and ruin it by sleeping with Blair’s best friend, Serena (Blake Lively) — on top of a hotel bar, nonetheless — after getting drunk at a wedding. Classy, you two. Real classy.