Sideways (2004)

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High school teacher and wine connoisseur Miles Raymond celebrates the impending marriage of his actor friend Jack by driving the pair of them off to California wine country for seven days of alcohol, food and golf. Jack intends to use the break for one final fling before tying the knot, and he is determined to find Miles a partner too. The perfect woman for Miles seems to be waitress Maya. However, Miles's lack of self-confidence continually stymies any romantic overtures.