Who Has Leighton Meester Dated? A Relationship Timeline

When we think of Leighton Meester’s love life, we have to assume it’s much like her Gossip Girl alter ego Blair Waldorf’s — you know, secret trysts, hot limo sex, and being tied up with expensive bowties. But although the former teen screen queen had lots of onscreen sex with Ed Westwick’s Chuck Bass, and only occasionally deviated, her real life has been a little different.

"I never had a boyfriend until I was 18. It's nice, I guess — when you like them," she told Marie Claire (via Us Weekly) in 2012. "But it isn't the most important thing." So, which guys have made the cut and which fell into the “Guys who weren’t Chuck Bass so who cares” category? Flip through to take a walk down Leighton’s memory lane.