Character: Gray

Directed by: Susannah Grant

Written by: Susannah Grant

Cast Members: Timothy Olyphant, Kevin Smith, Juliette Lewis, Sam Jaeger

Released date: January 26, 2006

Genre: Comedy, Drama, Romance

After the sudden death of her fiancé, Gray Wheeler finds comfort in the company of his friends: lighthearted and comic Sam, hyper-responsible Dennis, and, oddly enough, his old childhood buddy Fritz, 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.

Notable Mentions
• Jennifer was pregnant with her first daughter, Violet, while filming.
• Jennifer would reunite with Juliette Lewis for HBO’s Camping (2018).