Who Has Leighton Meester Dated? A Relationship Timeline

Though Sebastian Stan had a brief stint on Gossip Girl as bad boy billionaire Carter Baizen, the only lips he kissed were Serena’s (Blake Lively), not Blair’s (Leighton Meester). IRL, Leighton and Sebastian dated for a couple years and were super couply. Read: double dates in Jamaica with Ed Westwick (Chuck Bass) and Jessica Szohr (Vanessa), gifts of art, and the like. Leighton told Us Weekly that her “best friend” slash boyfriend put a ton of thought into the painting he gifted her. "He told the artist about me, my favorite colors and poetry and she painted a large very special abstract work I have hanging in my dining room," she says of the lavish gift.

But despite all the gushing and the general attractiveness of the couple, Leighton called it quits with her actor boyfriend in April 2010. An insider told OK Magazine at the time, Leighton "doesn't know how to be in a relationship and doesn't really like them."