- Two men reaching middle age with not much to show but disappointment embark on a week-long road trip through California's wine country, just as one is about to take a trip down the aisle.
- A week before his friend Jack is to be married, best man Miles and the prospective groom head off to wine country for a week of fun, relaxation and - of course - wine drinking. Miles is the oenophile and does his best to teach Jack a bit about the art of appreciating great wine. All Jack cares about is drinking and carousing, something he accomplishes when he meets the attractive Stephanie at one of the vineyards. Miles is something of a sad sack, a high school English teacher who is a failed writer at heart. He has yet to get over the fact that his wife has divorced him and that she has remarried and he now faces that nerve racking wait for word from a prospective publisher. Miles has an opportunity to start anew when he meets Stephanie's friend Maya but when he lets slip that Jack is about to be married any hope of a relationship seems to be lost.—garykmcd
- Miles Raymond is a hopeful but struggling writer who also happens to be a wine connoisseur. Jack Cole is a fading actor and his soon-to-be married friend. To celebrate Jack's concluding days as a bachelor, they will embark on a wine-tasting road trip through California's renowned vineyards. As they travel through the countryside, the two men confront their trepidation about what their futures hold and contemplate the paths in which they want to follow.—Kyle Perez
- Both approaching middle age, Miles is Jack's best man at his upcoming wedding. A middle school English teacher, Miles is a depressed and thus depressive sad sack, ever since the divorce from his wife, Victoria, two years ago, she who he still loves. He has just completed his third novel which took three years out of his life, he, in his negative outlook on his life in general, believes it will go the way of the unpublished first two: nowhere. Jack, an actor with some fame, has an easy charm which fronts his overgrown adolescent mentality. The two men plan to take a road trip just before the wedding from their home in San Diego to California wine country as a week long bachelor party, it a region that Miles often visits as a wine connoisseur. It isn't until they arrive that against Miles' plans to enjoy and educate Jack on the detailed pleasures of wine while they hang out together, Jack informs him that his number one goal for this trip is to get laid, and while unspoken, not necessarily the last time with someone else other than his fiancée, Christine, and that even if Miles does not approve, he better not mess up this week for him in his depressive state scaring off any potential sex partners. As such, Jack arranges for them to hang out with Stephanie, who they meet in she working behind the bar at one of the wineries, and Maya, Stephanie's friend who works as a server at a restaurant where Miles often hangs out, who Miles has a casual acquaintanceship with already, and who Jack can see is interested in Miles. While the rest of the week with Maya and Stephanie doesn't go quite the way either Miles or Jack anticipates, it may provide them with a tipping point for moving forward with their immediate futures.—Huggo
- Feeling humbled by his disastrous divorce two years ago, Miles Raymond, an unfulfilled English teacher and unpublished novelist, wants to escape his miserable existence. And now that his long-time playboy friend and ageing voice-over actor Jack Cole has finally decided to tie the knot, the wounded oenophile treats his old college buddy to a stag weekend in sunny California's wine country. You see, Miles plans to introduce husband-to-be Jack to the world of fine wine a few days before his wedding. However, while Miles tries to discover the distinctive scent of perfection captured in a bottle of expensive Pinot Noir, flirtatious Jack, who happily drinks cheap Merlot, has other plans: he is bent on scoring one last time before giving up his freedom. As the mismatched companions embark on a grape-scented bonding trip in Miles' 1987 Saab 900 Convertible Turbo, sex gets in the way of happiness, putting their friendship to the test. When love goes sideways, is there a remedy for broken hearts?—Nick Riganas
- Miles Raymond (Paul Giamatti) is an unsuccessful writer, a wine-aficionado, and a depressed middle school English teacher living in San Diego, who takes his soon-to-be-married actor friend and college roommate, Jack Cole (Thomas Haden Church), on a road trip through Santa Ynez Valley wine country. Miles wants to relax and live well. However, Jack wants one last sexual fling.
In the wine country, the men encounter Maya (Virginia Madsen), a waitress at Miles's favorite restaurant, The Hitching Post, and her friend, Stephanie (Sandra Oh), an employee at a local winery. They arrange a double date without revealing that Jack is to be married. Jack has an affair with Stephanie while Miles and Maya connect. Miles accidentally tells Maya that Jack is to be married. Enraged by the dishonesty, Maya dumps Miles and tells Stephanie, who breaks Jack's nose using her motorcycle helmet.
Upon finding out his manuscript has been rejected again, Miles makes a scene at a wine tasting room, and Jack hooks up with another waitress named Cammi. Jack gets into deeper trouble when Cammi's husband comes home unexpectedly & has to flee without his clothes and wallet (which contains the wedding rings). Miles sneaks into Cammi's house and barely escapes with Jack's wallet. To explain the broken nose to his fiancée, Jack runs Miles's car into a ditch to create front-end damage and tells her that he was hurt in an accident.
At the wedding, Miles runs into his ex-wife Vicki and meets her new husband. After learning that she is also pregnant, Miles faces the fact that Vicki will never return to him. Alone, he drinks his prized wine, a 1961 Château Cheval Blanc from a disposable coffee cup at a fast-food restaurant. Later, he receives a message from Maya, who says she enjoyed his manuscript and invites him to visit. The last scene in the movie shows Miles back in Santa Ynez, knocking on Maya's door.
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