After the sudden death of her fiance, Gray Wheeler (Garner) finds comfort in the company of his friends: lighthearted and comic Sam (Kevin Smith), hyper responsible Dennis (Sam Jager) and, oddly enough, his old childhood buddy Fritz (Timothy Olyphant), an irresponsible playboy whom she'd previously pegged as one of the least reliable people in the world. As secrets about her supposedly perfect fiance emerge, Gray comes to see new sides of the man she though she knew, and at the same time, finds herself drawn to the last man she ever expected to fall for.