 Miles is a failed writer living a meager existence in San Diego as an English teacher. With his career seemingly fading and the fate of a book hinging on a publisher s decision, Miles is depressed with himself and what he hasn t achieved. Jack is a television actor whom some recognize but not many do, as if he were a minor actor who got a taste of success. With his best friend Miles, the two embark on a road trip through California s wine country. Miles wants to give his friend a nice sendoff before married life, while Jack simply wants to have a fling beforehand. As they re both nearing middle age with not much to show for it, the two will explore the vineyards while ultimately searching for their identities.