The seeds of love are planted when Lisa, a high-powered investment banker, receives flowers from a secret admirer. But when his fairy-tale fantasies clash with her workaholic ways, they soon find out that sometimes, it's harder than it seems for love to conquer all.

A troubled woman seeks out the child she gave up for adoption; a gay motel owner takes in a handsome drifter; and the wife of a preacher frets that a gay couple has moved in across the street. All of their lives will intersect as Loggerheads subtly draws out their secret losses and desires.