15 TV Characters Who Can't Keep Their Pants On (PHOTOS)

Map out all the hookups and relationships in Gossip Girl’s four seasons and you’ll end up with one tangled web. While Serena (Blake Lively), Nate (Chace Crawford), and Dan (Penn Badgley) have enjoyed plenty of Upper East Side action over the years, the worst offender has to be billionaire playboy Chuck Bass (Ed Westwick). When not hung up on Blair Waldorf (Leighton Meester), Chuck occupies himself with booze, drugs, and prostitutes. Okay, let’s be real — he does that even when he is lusting after our Queen B.

Bottom line: He’s lost a bit of his edge over the years, but he’ll always be Chuck Bass — a ridiculously wealthy 20-something with money to spend and people to do.