Depressed wine enthusiast Miles (Paul Giamatti) takes his handsome friend Jack (Thomas Haden Church) on a tour of California wineries just before Jack ties the knot. The trip starts as just two guys on the road and a fair amount of alcohol, but when Miles explores his feelings for a pretty waitress (Virginia Madsen) and Jack considers a fling with a flirty pour girl (Sandra Oh), situations get complicated. With midlife crises on the horizon and too much wine in their stomachs, Miles and Jack must figure out where they’re going and what they want out of life before the next big crossroads.