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* MyGirlIsASlut: Suffice to say that the waitress's husband is a lot less angry with her for stepping out on him with Jack than you'd normally expect.
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Middle-aged [[HeterosexualLifePartners BFFs]] Miles (Creator/PaulGiamatti) and Jack (Creator/ThomasHadenChurch) take off to California's wine country for the week as Miles's gift to Jack before he is to be married on Saturday with Miles as best man. Both, however, have a hidden agenda: Miles [[DrowningMySorrows just wants to drink]] as he's clinically depressed about his divorce (two years and counting) and failure to get his novels published; Jack wants to get laid one more time before settling down with one woman. During the week, they encounter two women: one is Maya (Creator/VirginiaMadsen), a kind-hearted, beautiful, and intelligent woman who Miles has longed after for a while (not in the least because she's just as knowledgeable about wine as he is) but CanNotSpitItOut. The other is Stephanie (Creator/SandraOh), a spirited MILF wine pourer who instantly takes Jack up on his charming advances.

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Middle-aged [[HeterosexualLifePartners BFFs]] Miles (Creator/PaulGiamatti) and Jack (Creator/ThomasHadenChurch) take off to California's wine country for the week as Miles's gift to Jack before he is to be married on Saturday with Miles as best man. Both, however, have a hidden agenda: Miles [[DrowningMySorrows just wants to drink]] as he's clinically depressed about his divorce (two years and counting) and failure to get his novels published; Jack wants to get laid one more time before settling down with one woman. During the week, they encounter two women: one is Maya (Creator/VirginiaMadsen), a kind-hearted, beautiful, and intelligent woman who Miles has longed after for a while (not in the least because she's just as knowledgeable about wine as he is) but CanNotSpitItOut. The other is Stephanie (Creator/SandraOh), a spirited MILF spirited, adventurous, wine pourer who instantly takes Jack up on his charming advances.
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* WeddingRingDefense: Discussed by Jack (who provides that page quote).

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* WeddingRingDefense: Discussed by Jack. Miles is reluctant to talk to Maya initially because last time they spoke she was wearing a ring. Jack (who provides says that page quote). his current fiancee Christine did, too, but it was just to ward off unwanted suitors and he wasn't fooled--"How do you think ''I'' met her?" He later informs Miles that Maya doesn't have the ring on anymore.

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Middle-aged [[HeterosexualLifePartners BFFs]] Miles (Creator/PaulGiamatti) and Jack (Creator/ThomasHadenChurch) take off to California's wine country for the week as Miles's gift to Jack before he is to be married on Saturday with Miles as best man. Both, however, have a hidden agenda: Miles [[DrowningMySorrows just wants to drink]] as he's clinically depressed about his divorce (two years and counting) and failure to get his novels published; Jack [[OneLastFling wants to get laid one more time]] before settling down with one woman. During the week, they encounter two women: one is Maya (Creator/VirginiaMadsen), a kind-hearted, beautiful, and intelligent woman who Miles has longed after for a while (not in the least because she's just as knowledgeable about wine as he is) but CanNotSpitItOut. The other is Stephanie (Creator/SandraOh), a spirited MILF wine pourer who instantly takes Jack up on his charming advances.

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Middle-aged [[HeterosexualLifePartners BFFs]] Miles (Creator/PaulGiamatti) and Jack (Creator/ThomasHadenChurch) take off to California's wine country for the week as Miles's gift to Jack before he is to be married on Saturday with Miles as best man. Both, however, have a hidden agenda: Miles [[DrowningMySorrows just wants to drink]] as he's clinically depressed about his divorce (two years and counting) and failure to get his novels published; Jack [[OneLastFling wants to get laid one more time]] time before settling down with one woman. During the week, they encounter two women: one is Maya (Creator/VirginiaMadsen), a kind-hearted, beautiful, and intelligent woman who Miles has longed after for a while (not in the least because she's just as knowledgeable about wine as he is) but CanNotSpitItOut. The other is Stephanie (Creator/SandraOh), a spirited MILF wine pourer who instantly takes Jack up on his charming advances.



* OneLastFling: Jack's mission for the trip.
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-->'''Jack'': ''[radio voice]'' Consult your doctor before using this product, side effects may include oily discharge, hives, loss of appetite, low blood pressure, if you have diabetes or a history of kidney trouble...''you're dead, asshole!''

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-->'''Jack'': -->'''Jack''': ''[radio voice]'' Consult your doctor before using this product, side effects may include oily discharge, hives, loss of appetite, low blood pressure, if you have diabetes or a history of kidney trouble...''you're dead, asshole!''
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* RattlingOffLegal: Jack mentions to Maya that he mainly does "voiceover" roles currently, and reveals this trope is his particular work.
-->'''Jack''': ''[radio voice]'' Now with a low, low 5.9% APR financing!
-->'''Maya''': That's hilarious, you sound just like one of those guys!
-->'''Jack''': I ''am'' one of those guys!
-->'''Maya''': You are ''not''!
-->'''Jack'': ''[radio voice]'' Consult your doctor before using this product, side effects may include oily discharge, hives, loss of appetite, low blood pressure, if you have diabetes or a history of kidney trouble...''you're dead, asshole!''

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* BigBeautifulWoman: The waitress at the barbeque restaurant. ('Betcha that chick's two tons of fun.')

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* BigBeautifulWoman: The waitress at the barbeque restaurant. ('Betcha restaurant; Jack ''immediately'' (and successfully) hits on her.
-->'''Jack''': Betcha
that chick's two tons of fun.')fun, you know, the grateful type.
-->'''Miles''': ''[annoyed]'' I wouldn't know about that.


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* ContrivedCoincidence: Stephanie, a wine pourer who serves Miles and Jack during their tour of Santa Barbara wine country, somehow just so happens to be friends with Hitching Post waitress Maya back in Buellton, whom Miles already knows from his past visits, setting up the main quartet of characters.
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* INeedToGoIronMyDog: While the quartet are out to dinner, Miles gets hammered and drunkenly dials his ex-wife for a bitter conversation about her impending marriage. When he comes back to the table, he's visibly irritated, which leaves an awkward silence around the table. Stephanie silently signals to Maya to go to the bathroom with her right then so that Jack and Miles can hash things out alone.
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* ICanExplain: Jack [[spoiler: while Stephanie beats him down with her motorcycle helmet]] to no avail.



-->'''Stephanie''': [[spoiler: ''[angry]'' You're getting married on Saturday?! What the fuck! ''[sobbing]'' You said you loved me! ''[angry]'' I HOPE YOU DIE!]]

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-->'''Stephanie''': [[spoiler: ''[angry]'' You're getting married on Saturday?! What the fuck! about that shit you said to me! ''[sobbing]'' You said you loved me! ''[angry]'' I HOPE YOU DIE!]]
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* MoodWhiplash: Stephanie [[spoiler: while beating the crap out of Jack once she knows the truth about him.]]
-->'''Stephanie''': [[spoiler: ''[angry]'' You're getting married on Saturday?! What the fuck! ''[sobbing]'' You said you loved me! ''[angry]'' I HOPE YOU DIE!]]
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* DVDCommentary: Giamatti and Church do one for the film that is almost as hilarious as the film itself, thanks to their endless SelfDeprecation.



* TheSmurfettePrinciple: Averted in that the two women in the story are crucial in the CharacterDevelopment for the two male leads.
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* BlatantLies: Miles tends to resort to lying whenever he makes a mistake (usually the result of his drinking). Jack has known Miles long enough to see through him.

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* BlatantLies: Both Miles tends to resort to lying whenever he makes a mistake (usually the result of his drinking). and Jack has are prone to telling lies to cover up their less admirable qualities (Miles' drinking and Jack's philandering). The two friends have known Miles each long enough to see through him.them.
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* AmbiguousSituation: Early on, it is established that not only is Miles prone to lying to cover up his drunken shortcomings, but Jack is able to see through them. [[spoiler: After Stephanie breaks Jack's nose, Miles denies telling Maya about the wedding, and pins the blame on a bartender they spoke to earlier. Jack mulls it over and doesn't seem to buy it. Wrecking Miles' car to explain the broken nose may have also been Jack's way of getting back at Miles.]]


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* BlatantLies: Miles tends to resort to lying whenever he makes a mistake (usually the result of his drinking). Jack has known Miles long enough to see through him.
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* NasalTrauma: Jack gets smashed him in the face by a motorcyle helmet-wielding Stephanie, breaking his nose. He spends the rest of the film wearing a nasal splint, and has to crash Miles' car into a tree to make it look as if they've been in an accident.
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[[HilarityEnsues Hilarity]], BittersweetEnding and bittersweetness]] ensue. (And wine drinking. Lots and lots of wine drinking.)

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[[HilarityEnsues Hilarity]], BittersweetEnding [[BittersweetEnding and bittersweetness]] ensue. (And wine drinking. Lots and lots of wine drinking.)
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Middle-aged [[HeterosexualLifePartners BFFs]] Miles (Creator/PaulGiamatti) and Jack (Thomas Haden Church) take off to California's wine country for the week as Miles's gift to Jack before he is to be married on Saturday with Miles as best man. Both, however, have a hidden agenda: Miles [[DrowningMySorrows just wants to drink]] as he's clinically depressed about his divorce (two years and counting) and failure to get his novels published; Jack [[OneLastFling wants to get laid one more time]] before settling down with one woman. During the week, they encounter two women: one is Maya (Creator/VirginiaMadsen), a kind-hearted, beautiful, and intelligent woman who Miles has longed after for a while (not in the least because she's just as knowledgeable about wine as he is) but CanNotSpitItOut. The other is Stephanie (Creator/SandraOh), a spirited MILF wine pourer who instantly takes Jack up on his charming advances.

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Middle-aged [[HeterosexualLifePartners BFFs]] Miles (Creator/PaulGiamatti) and Jack (Thomas Haden Church) (Creator/ThomasHadenChurch) take off to California's wine country for the week as Miles's gift to Jack before he is to be married on Saturday with Miles as best man. Both, however, have a hidden agenda: Miles [[DrowningMySorrows just wants to drink]] as he's clinically depressed about his divorce (two years and counting) and failure to get his novels published; Jack [[OneLastFling wants to get laid one more time]] before settling down with one woman. During the week, they encounter two women: one is Maya (Creator/VirginiaMadsen), a kind-hearted, beautiful, and intelligent woman who Miles has longed after for a while (not in the least because she's just as knowledgeable about wine as he is) but CanNotSpitItOut. The other is Stephanie (Creator/SandraOh), a spirited MILF wine pourer who instantly takes Jack up on his charming advances.
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[[HilarityEnsues Hilarity]], [[CrowningMomentOfHeartwarming heartwarming]], [[BittersweetEnding and bittersweetness]] ensue. (And wine drinking. Lots and lots of wine drinking.)

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[[HilarityEnsues Hilarity]], [[CrowningMomentOfHeartwarming heartwarming]], [[BittersweetEnding BittersweetEnding and bittersweetness]] ensue. (And wine drinking. Lots and lots of wine drinking.)
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* NakedPeopleAreFunny: The scene in which Miles has to retrieve Jack's wallet, walks in on a couple having sex and is chased off by the naked husband. Giamatti noted this trope is the only way Alexander Payne will put a sex scene or nudity in his movie (see also: ''AboutSchmidt'').

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* NakedPeopleAreFunny: The scene in which Miles has to retrieve Jack's wallet, walks in on a couple having sex and is chased off by the naked husband. Giamatti noted this trope is the only way Alexander Payne will put a sex scene or nudity in his movie (see also: ''AboutSchmidt'').''Film/AboutSchmidt'').
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* ActorAllusion: Thomas Haden Church's character is a former TV star now doing commercial voiceovers, which mirrors Church's own career.
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* BewareTheNiceOnes: Stephanie is spirited and kind, but she ''did'' break Jack's nose when she figured out the truth.

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* BerserkButton: Miles will ''not'' drink any [[PrecisionFStrike fucking]] Merlot. He'd also appreciate it if you didn't bring up his wife getting re-married or his affair during that marriage.



* BerserkButton: Miles will ''not'' drink any [[PrecisionFStrike fucking]] Merlot. He'd also appreciate it if you didn't bring up his wife getting re-married or his affair during that marriage.
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Middle-aged [[HeterosexualLifePartners BFFs]] Miles (Creator/PaulGiamatti) and Jack (Thomas Haden Church) take off to California's wine country for the week as Miles's gift to Jack before he is to be married on Saturday with Miles as best man. Both, however, have a hidden agenda: Miles [[DrowningMySorrows just wants to drink]] as he's clinically depressed about his divorce (two years and counting) and failure to get his novels published; Jack [[OneLastFling wants to get laid one more time]] before settling down with one woman. During the week, they encounter two women: one is Maya (Creator/VirginiaMadsen), a kind-hearted, beautiful, and intelligent woman who Miles has longed after for a while (not in the least because she's just as knowledgeable about wine as he is) but CanNotSpitItOut. The other is Stephanie (Sandra Oh), a spirited MILF wine pourer who instantly takes Jack up on his charming advances.

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Middle-aged [[HeterosexualLifePartners BFFs]] Miles (Creator/PaulGiamatti) and Jack (Thomas Haden Church) take off to California's wine country for the week as Miles's gift to Jack before he is to be married on Saturday with Miles as best man. Both, however, have a hidden agenda: Miles [[DrowningMySorrows just wants to drink]] as he's clinically depressed about his divorce (two years and counting) and failure to get his novels published; Jack [[OneLastFling wants to get laid one more time]] before settling down with one woman. During the week, they encounter two women: one is Maya (Creator/VirginiaMadsen), a kind-hearted, beautiful, and intelligent woman who Miles has longed after for a while (not in the least because she's just as knowledgeable about wine as he is) but CanNotSpitItOut. The other is Stephanie (Sandra Oh), (Creator/SandraOh), a spirited MILF wine pourer who instantly takes Jack up on his charming advances.
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* AdaptationNameChange: In the novel, Maya's friend is named Terra. In the film, her name is changed to Stephanie.
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* NiceGirl: Both Maya and Stephanie. Even though Stephanie can still bust Jack's nose when she discovers the truth.
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* ComicallyMissingThePoint: [[spoiler: After learning his latest novel will not be published,]] Miles bemoans that he's so insignificant that he cannot commit suicide. Instead of sympathetic uplifting, Jack helpfully points out that John Kennedy Toole of ''AConfederacyOfDunces'' committed suicide [[spoiler: before he was published.]]

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* ComicallyMissingThePoint: [[spoiler: After learning his latest novel will not be published,]] Miles bemoans that he's so insignificant that he cannot commit suicide. Instead of sympathetic uplifting, Jack helpfully points out that John Kennedy Toole of ''AConfederacyOfDunces'' ''Literature/AConfederacyOfDunces'' committed suicide [[spoiler: before he was published.]]

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[[quoteright:350:http://static.tvtropes.org/pmwiki/pub/images/sideways.jpg]]

A 2004 [[{{Dramedy}} comedy/drama]] directed and co-written by Creator/AlexanderPayne. Middle-aged [[HeterosexualLifePartners BFFs]] Miles (Creator/PaulGiamatti) and Jack (Thomas Haden Church) take off to California's wine country for the week as Miles's gift to Jack before he is to be married on Saturday with Miles as best man. Both, however, have a hidden agenda: Miles [[DrowningMySorrows just wants to drink]] as he's clinically depressed about his divorce (two years and counting) and failure to get his novels published; Jack [[OneLastFling wants to get laid one more time]] before settling down with one woman. During the week, they encounter two women: one is Maya (Creator/VirginiaMadsen), a kind-hearted, beautiful, and intelligent woman who Miles has longed after for a while (not in the least because she's just as knowledgeable about wine as he is) but CanNotSpitItOut. The other is Stephanie (Sandra Oh), a spirited MILF wine pourer who instantly takes Jack up on his charming advances. [[HilarityEnsues Hilarity]], [[CrowningMomentOfHeartwarming heartwarming]], [[BittersweetEnding and bittersweetness ensues.]] And wine drinking. Lots of it.

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[[quoteright:350:http://static.[[quoteright:300:http://static.tvtropes.org/pmwiki/pub/images/sideways.jpg]]

org/pmwiki/pub/images/sideways_2004.jpg]]

A 2004 [[{{Dramedy}} comedy/drama]] film directed and co-written by Creator/AlexanderPayne. Creator/AlexanderPayne.

Middle-aged [[HeterosexualLifePartners BFFs]] Miles (Creator/PaulGiamatti) and Jack (Thomas Haden Church) take off to California's wine country for the week as Miles's gift to Jack before he is to be married on Saturday with Miles as best man. Both, however, have a hidden agenda: Miles [[DrowningMySorrows just wants to drink]] as he's clinically depressed about his divorce (two years and counting) and failure to get his novels published; Jack [[OneLastFling wants to get laid one more time]] before settling down with one woman. During the week, they encounter two women: one is Maya (Creator/VirginiaMadsen), a kind-hearted, beautiful, and intelligent woman who Miles has longed after for a while (not in the least because she's just as knowledgeable about wine as he is) but CanNotSpitItOut. The other is Stephanie (Sandra Oh), a spirited MILF wine pourer who instantly takes Jack up on his charming advances.

[[HilarityEnsues Hilarity]], [[CrowningMomentOfHeartwarming heartwarming]], [[BittersweetEnding and bittersweetness ensues.]] And bittersweetness]] ensue. (And wine drinking. Lots and lots of it. wine drinking.)
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A 2004 comedy/drama directed and co-written by Creator/AlexanderPayne. Middle-aged [[HeterosexualLifePartners BFFs]] Miles (Creator/PaulGiamatti) and Jack (Thomas Haden Church) take off to California's wine country for the week as Miles's gift to Jack before he is to be married on Saturday with Miles as best man. Both, however, have a hidden agenda: Miles [[DrowningMySorrows just wants to drink]] as he's clinically depressed about his divorce (two years and counting) and failure to get his novels published; Jack [[OneLastFling wants to get laid one more time]] before settling down with one woman. During the week, they encounter two women: one is Maya (Creator/VirginiaMadsen), a kind-hearted, beautiful, and intelligent woman who Miles has longed after for a while (not in the least because she's just as knowledgeable about wine as he is) but CanNotSpitItOut. The other is Stephanie (Sandra Oh), a spirited MILF wine pourer who instantly takes Jack up on his charming advances. [[HilarityEnsues Hilarity]], [[CrowningMomentOfHeartwarming heartwarming]], [[BittersweetEnding and bittersweetness ensues.]] And wine drinking. Lots of it.

to:

A 2004 comedy/drama [[{{Dramedy}} comedy/drama]] directed and co-written by Creator/AlexanderPayne. Middle-aged [[HeterosexualLifePartners BFFs]] Miles (Creator/PaulGiamatti) and Jack (Thomas Haden Church) take off to California's wine country for the week as Miles's gift to Jack before he is to be married on Saturday with Miles as best man. Both, however, have a hidden agenda: Miles [[DrowningMySorrows just wants to drink]] as he's clinically depressed about his divorce (two years and counting) and failure to get his novels published; Jack [[OneLastFling wants to get laid one more time]] before settling down with one woman. During the week, they encounter two women: one is Maya (Creator/VirginiaMadsen), a kind-hearted, beautiful, and intelligent woman who Miles has longed after for a while (not in the least because she's just as knowledgeable about wine as he is) but CanNotSpitItOut. The other is Stephanie (Sandra Oh), a spirited MILF wine pourer who instantly takes Jack up on his charming advances. [[HilarityEnsues Hilarity]], [[CrowningMomentOfHeartwarming heartwarming]], [[BittersweetEnding and bittersweetness ensues.]] And wine drinking. Lots of it.
Is there an issue? Send a MessageReason:
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A 2004 comedy/drama. Middle-aged [[HeterosexualLifePartners BFFs]] Miles (Creator/PaulGiamatti) and Jack (Thomas Haden Church) take off to California's wine country for the week as Miles's gift to Jack before he is to be married on Saturday with Miles as best man. Both, however, have a hidden agenda: Miles [[DrowningMySorrows just wants to drink]] as he's clinically depressed about his divorce (two years and counting) and failure to get his novels published; Jack [[OneLastFling wants to get laid one more time]] before settling down with one woman. During the week, they encounter two women: one is Maya (Virginia Madsen), a kind-hearted, beautiful, and intelligent woman who Miles has longed after for a while (not in the least because she's just as knowledgeable about wine as he is) but CanNotSpitItOut. The other is Stephanie (Sandra Oh), a spirited MILF wine pourer who instantly takes Jack up on his charming advances. [[HilarityEnsues Hilarity]], [[CrowningMomentOfHeartwarming heartwarming]], [[BittersweetEnding and bittersweetness ensues.]] And wine drinking. Lots of it.

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A 2004 comedy/drama.comedy/drama directed and co-written by Creator/AlexanderPayne. Middle-aged [[HeterosexualLifePartners BFFs]] Miles (Creator/PaulGiamatti) and Jack (Thomas Haden Church) take off to California's wine country for the week as Miles's gift to Jack before he is to be married on Saturday with Miles as best man. Both, however, have a hidden agenda: Miles [[DrowningMySorrows just wants to drink]] as he's clinically depressed about his divorce (two years and counting) and failure to get his novels published; Jack [[OneLastFling wants to get laid one more time]] before settling down with one woman. During the week, they encounter two women: one is Maya (Virginia Madsen), (Creator/VirginiaMadsen), a kind-hearted, beautiful, and intelligent woman who Miles has longed after for a while (not in the least because she's just as knowledgeable about wine as he is) but CanNotSpitItOut. The other is Stephanie (Sandra Oh), a spirited MILF wine pourer who instantly takes Jack up on his charming advances. [[HilarityEnsues Hilarity]], [[CrowningMomentOfHeartwarming heartwarming]], [[BittersweetEnding and bittersweetness ensues.]] And wine drinking. Lots of it.
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* DoubleMeaningTitle: The title refers to the way wine is stored, and that both the main characters are sort of stuck, holding on to unhealthy and immature behaviors.

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