Both approaching middle age, Miles is Jack's best man at his upcoming wedding. A middle school English teacher, Miles is a depressed and thus depressive sad sack, ever since the divorce from his wife, Victoria, two years ago, she who he still loves. He has just completed his third novel which took three years out of his life, he, in his negative outlook on his life in general, believes it will go the way of the unpublished first two: nowhere. Jack, an actor with some fame, has an easy charm which fronts his overgrown adolescent mentality. The two men plan to take a road trip just before the wedding from their home in San Diego to California wine country as a week long bachelor party, it a region that Miles often visits as a wine connoisseur. It isn't until they arrive that against Miles' plans to enjoy and educate Jack on the detailed pleasures of wine while they hang out together, Jack informs him that his number one goal for this trip is to get laid, and while unspoken, not necessarily the last time with someone else other than his fiancée, Christine, and that even if Miles does not approve, he better not mess up this week for him in his depressive state scaring off any potential sex partners. As such, Jack arranges for them to hang out with Stephanie, who they meet in she working behind the bar at one of the wineries, and Maya, Stephanie's friend who works as a server at a restaurant where Miles often hangs out, who Miles has a casual acquaintanceship with already, and who Jack can see is interested in Miles. While the rest of the week with Maya and Stephanie doesn't go quite the way either Miles or Jack anticipates, it may provide them with a tipping point for moving forward with their immediate futures.
Oscar Writing (Adapted Screenplay) 2005
Nominated for Best Picture 2005
Nominated for Actor in a Supporting Role 2005 (Thomas Haden Church)
Nominated for Actress in a Supporting Role 2005 (Virginia Madsen)
Nominated for Directing 2005 (Alexander Payne)