Who Has Leighton Meester Dated? A Relationship Timeline

The ridiculously-named Chiles Stanton and Beau Hutton sang together in Country Strong, and man, it was a lot to watch. Although they played rivals in the movie, they eventually ended up together. In real life, rumor had it there was a lot more loving than hating happening. An insider told Us Weekly in January 2011 that the two were “inseparable the entire night” at an HBO-hosted Golden Globes after party.

The insider claimed, "Garrett wrapped his arm around her. She wraps her arm completely around his neck and pulls him for a quick peck on the lips." While the two never confirmed anything, Leighton does love a little co-star cuddling, so...