From supermodel to supermodel to Gossip Girl to supermodel. Leo loves the ladies! Though currently dating Victoria’s Secret model Tori Garrn, 20, his ex-girlfriends list includes Blake Lively, Bar Refaeli, and Gisele Bundchen. Leo's never at a loss for beautiful women to be by his side. As recent as last month, he was yachting with a bevy of gorgeous women in Cannes. Tough life!