After the sudden death of her fiance, Gray Wheeler (Jennifer Garner) finds comfort in the company of her late love's friends Sam (Kevin Smith), Dennis (Sam Jaeger) and his old childhood buddy Fritz (Timothy Olyphant from TV'S Deadwood) - an irresponsible playboy whom she'd previously thought of as the least reliable person in the world. But as secrets begin to emerge about her supposedly perfect fiance, Gray comes to see new sides of the man she thought she knew....and finds herself drawn to the last man she ever expected to fall for.