Catch and Release (2007)

After the sudden death of her fiancé, Gray Wheeler (Jennifer Garner) finds comfort in the company of his friends: lighthearted and comic Sam (Kevin Smith), hyper-responsible Dennis (Sam Jaeger), 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 fiancé emerge, Gray comes to see new sides of the man she thought she knew, and at the same time, finds herself drawn to the last man she ever expected to fall for.