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| Paul Giamatti | Miles Raymond |
| Thomas Haden Church | Jack Lopate |
| Virginia Madsen | Maya |
| Sandra Oh | Stephanie |
| Marylouise Burke | Miles' Mother |
| Jessica Hecht | Victoria |
| Missy Doty | Cammie |
| M.C. Gainey | Cammi's Husband |
| Patrick Gallagher | Gary the Bartender |
| Alex Kalognomos | Alex Erganian |
| Joe Marinelli | Pourer |
| Alysia Reiner | Christine |
Struggling writer and wine enthusiast Miles takes his engaged friend, Jack, on a trip to wine country for a last single-guy bonding experience. While Miles wants to relax and enjoy the wine, Jack is in search of a fling before his wedding. Soon Jack is sleeping with Stephanie, while her friend Maya connects with Miles. When Miles lets slip that Jack is getting married, both women are furious, sending the trip into disarray.
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