A wine tasting road trip to salute Jack's (Thomas Haden Church) final days as a bachelor careens woefully sideways as he and Miles (Paul Giamatti) hit the gas en route to mid-life crises. The comically mismatched pair, who share little more than their history and a heady blend of failed potential and fading youth, soon find themselves drowning in wine and women (Sandra Oh and Virginia Madsen). Emerging from a haze of pinot noir, wistful yearnings and trepidation about the future, the two inevitably collide with reality.