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| Nia Vardalos | Genevieve |
| John Corbett | Greg |
| Stephen Guarino | Bill |
| Amir Arison | Bob |
| Zoe Kazan | Tammy Greenwood |
| Gary Wilmes | Cal |
| Mike Starr | John |
| Jason Mantzoukas | Brian |
| Judah Friedlander | Dan O'Finn |
| Rachel Dratch | Kathy Jeemy |
| Jay O. Sanders | Tim the Delivery Guy |
Genevieve, a florist, and Greg, a restaurateur, are relationship-challenged. Genevieve avoids the pain of a broken heart by never going out with a man more than five times, and Greg has a string of disastrous relationships behind him. Though Greg agrees to Genevieve's five-date rule, neither he nor Genevieve can predict the romantic sparks that fly when they get together.
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