 A week before the marriage of his great friend, the decadent actor Jack (Thomas Haden Church), the bitter frustrated writer divorced oenologist English teacher Miles Raymond (Paul Giamatti) 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 (Virginia Madsen) and the attendant Stephanie (Sandra Oh), 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.