Sideways

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.

A week before the marriage of his great friend, the decadent actor Jack, the bitter frustrated writer divorced oenologist English teacher Miles Raymond travels with him to the wine country of California to spend a week together. While Miles intends to drink wine and play golf, Jack indeed intends to score and get laid with as many women as possible. While hosted in the Windmill Inn, they meet the waitress Maya and the attendant Stephanie, and they spend some time together, visiting different wine makers and and Miles and Maya disclosing their inner secrets and falling in love for each other.

Miles Raymond, a failed writer and divorc? who teaches junior high school English takes his best friend, former hot actor Jack, on a weeklong drive up to California's wine country. There they explore the nature of their failures and question their relationships. Jack, 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 a relationship with the woman's best friend, a fellow oenophile who is a waitress at a restaurant that he frequents often when visiting that part of the country.