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NOTE: This spoiler was sent in by CDM. who says... "This film differs in small ways from the book it was adapted from. If you liked the movie I recommend the book."

Miles (Paul Giamatti) is a middle-school English teacher, divorced over one year but still struggling to come to terms with it. His real occupation is struggling, as yet unpublished novelist.

His buddy Jack (Thomas Haden Church) is an aging Lothario. A former daytime soap star that now makes a living in commercials and voice-over work. Jack is set to be married in a week and the two buddies from college are going to take a week long tour through the wine country of Southern California as Jack’s going away/bachelor party.

The two hit the road in Miles broken down Saab. They stop at Miles mother’s house to wish her a happy birthday. The two buddies do not intend on staying but Miles mother insists they have dinner. During the meal, Miles sneaks into his mother’s bedroom and steals a wad of $100 bills from a small false aerosol can safe she has tucked away. When Miles returns to the table the conversation turns to his ex-wife and we see very clearly that Miles has not gotten over her and his entire life has been fairly empty since the divorce.

The next morning Miles and Jack sneak out of the house and continue on their way. Miles is a wine connoisseur and is planning on enjoying the week discovering some new favorite wines and spending some time with Jack. They stop at a couple of wineries where we see that Miles has the entire wine-tasting  routine down and he tries to teach Jack what is to fully appreciate and enjoy wine. They discuss what makes the varieties different, what makes a good wine in Miles opinion, why wine is important (wine will be a metaphor for the characters throughout the film).

The pair stop for dinner in a favorite haunt of Miles. There they meet the waitress Maya. Jack is taken by her and more amazed that Miles apparently knows her well from previous trips to the wine country. Jack begins to pester his friend with questions about how well he knows her and we see that one of Jack’s aims on the trip is to help his friend out of the funk he has been in since the divorce.

The next day the twosome hit some more wineries. Jack chats up the pourer in one of the tasting rooms and we learn his other goal for the trip – to have one last fling before the wedding. Jack finds that the pourer, Stephanie, knows Maya and sets up a date for the four of them. Miles is not too into this plan. He’s not feeling confident enough to handle a date with Maya and he also does not want to aid Jack in cheating in his fiancée. Jack will not take no for an answer though and the date is set.

At dinner that evening Jack and Stephanie are getting along well. Miles is doing OK with Maya, but doing even better with the bottles of wine that are flowing freely at the table. Miles becomes drunk and ends up drunk dialing his ex-wife. The call goes predictably poorly and Miles mood is soured. The foursome continue the date at Stephanie’s place. Jack and Stephanie retire to the bedroom leaving Miles and Maya alone. Their time is mostly awkward except when Maya asks Miles why he enjoys Pinot Noir (his favorite wine) so much. Miles explains his fascination to her and in doing so explains himself as best he can as well. Maya does the same when explaining how she came to enjoy wine.

The date ends awkwardly for Miles and Maya, but he does give her a rough copy of his manuscript (important later).

Miles spend the next day alone as Jack is spending time now with Stephanie. Miles is becoming increasingly angry with Jack for leaving him alone and because Miles is also having to cover for Jack as his fiancée has been calling.

Miles and Jack reunite and have words. Jack tries to make Miles understand what he is doing and also tells him that his ex-wife has remarried and will be at the wedding with her new husband. Miles loses it but he and Jack talk it through. Miles forgives Jack somewhat and agrees to again go out with Maya and Stephanie. This time the date goes better and Maya and Miles sleep together.

The next day Miles is the happiest we have seen him and he and Maya are spending time together and getting along well. Maya asks if maybe he and Jack can stick around for the weekend and Miles lets slip that they have to get back for the rehearsal dinner. Having slipped, Miles confesses everything to Maya. She is ticked off and insists on going home immediately where she plans on calling Stephanie and telling her everything.

The next day Miles and Jack return from breakfast to find Stephanie waiting for them – Maya has told her everything and she takes her frustrations out on Jack’s face with her motorcycle helmet.

Stephanie leaves and Miles takes Jack to the emergency room. Miles lies to Jack about how Stephanie found out. It would seem that the carnal adventures are over but that evening at dinner Jack picks up a waitress in a steakhouse and goes home with her. He shows up at the hotel room naked and shivering the next morning. It seems the waitress was married and her husband returned from his night job early. Jack begs Miles to return with him as he left his wallet and inside were personalized wedding bands. Jack breaks down crying and we see some remorse for what he has done. The pair return and Miles retrieves the wallet in a hilarious scene.

Miles and Jack seem to be back on good standing and are ready to leave the week behind them and return for the wedding. The last thing Jack has to do is wreck Miles car (to explain his very injured face to his fiancée) and Miles is too tired to argue.

At the wedding all goes well until Miles runs into his ex-wife and her new husband prior to the reception. She drops the news on him that she is also pregnant. Miles loses it again and skips the reception to be alone in a burger joint with his prized bottle of wine – one he has been saving for years for a “special occasion”. His downfall seems complete.

Some time later Miles comes home after work to a message on his machine from Maya. She has finished his manuscript (a book that will not be published, as he found out during the trip) and loved it. She has forgiven him somewhat for the lies and expresses a wish that things had gone better for them. The movie ends as Miles makes his way to Maya’s and knocks on her door, ready to begin living again.

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