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| Woody Allen | Prof. Gabriel ''Gabe'' Roth |
| Mia Farrow | Judy Roth |
| Juliette Lewis | Rain |
| Blythe Danner | Rain's Mother |
| Judy Davis | Sally |
| Liam Neeson | Michael Gates |
| Sydney Pollack | Jack |
| Lysette Anthony | Sam |
| Cristi Conaway | Shawn Grainger |
| Tim Jerome | Paul |
| Ron Rifkin | Richard |
| Jerry Zaks | Dinner Party Guest |
| Bruce Jay Friedman | Peter Styles |
| Benno Schmidt | Judy's Ex-Husband |
Gabe and his wife, Judy, are shocked to discover that their best friends, Sally and Jack, are splitting up. Not only did they not see the breakup coming, but it makes them start to question their own relationship. While Gabe flirts with the idea of dating one of his college students, Sally and Jack discover that being single again isn't all its cracked up to be and contemplate getting back together.
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