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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 |
A divorced teacher and his soon-to-be-married friend ponder their lives and relationships during a road trip through California wine country.
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