January 21, 2005
Genre(s): Romantic Comedy, Drama
Miles Raymond wants more out of life, but he doesn't know how to get what he wants. Facing rejection after rejection when it comes to his writing, he agrees to spend a week touring the wine country in California with his best friend Jack. The trip takes place the week before Jack's marriage, and Miles promises the other man's future wife that he will look after him. Though Miles loves wine and the finer things in life, Jack seemingly only cares about enjoying his last little bit of freedom. When the two arrive at a winery, Jack arranges a double date for the two. While Miles looks forward to the date, he also wants to make sure that his friend doesn't do something he regrets. That simple date sets up the premise for the film, as Miles finds himself in trouble thanks to the actions of his friend. As the story unfolds, viewers begin wondering if Miles will ever find the happiness he deserves and if Jack will ever receive the comeuppance that he needs.