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| Ryan Reynolds | Will Hayes |
| Isla Fisher | April |
| Abigail Breslin | Maya Hayes |
| Rachel Weisz | Summer Hartley |
| Derek Luke | Russell T. McCormack |
| Elizabeth Banks | Emily |
| Kevin Kline | Hampton Roth |
| Kevin Corrigan | Simon |
| Adam Ferrara | Gareth |
| Liane Balaban | Kelly |
| Nestor Serrano | Arthur Robredo |
| Jaime Tirelli | Rafael |
| Alexie Gilmore | Olivia |
| Dale Leigh | Bill Clinton |
| Marc Bonan | Kevin |
Will Hayes, a thirtysomething Manhattanite, is in the middle of divorce proceedings when his young daughter asks him about his life before marriage, including how he met and fell in love with her mother. Will flashes back to 1992 and recounts his romances with three women, changing their names so that his daughter must guess which one became his wife.
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