Jack and Miles were college roommates, and despite their differences, they have been friends ever since. Jack is an actor, whose career high point is a stint as a soap opera regular. English teacher and oenophile Miles would much rather be a published novelist. Jack is about to get married, so depressed, divorced Miles suggests they hit the road for a week-long bachelor party amidst the rolling hillsides and gorgeous sunsets of wine country near Santa...
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Miles is a divorced man and a failed writer who teaches junior high English. He decides to take his best friend, somewhat famous actor Jack, on a weeklong drive through California's wine country. There they explore their failures and question their relationships. Jack, who is about to get married, has an affair with a woman and wonders whether he should call off his wedding. Miles questions whether or not he made the right choice while trying to form...