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| Zach Braff | Michael |
| Casey Affleck | Chris |
| Michael Weston | Izzy |
| Eric Christian Olsen | Kenny |
| Jacinda Barrett | Jenna |
| Rachel Bilson | Kim |
| Blythe Danner | Anna |
| Tom Wilkinson | Stephen |
| Lauren Lee Smith | Lisa |
| Marley Shelton | Arianna |
| Ellen David | Izzy's Mother |
| Harold Ramis | Professor Bowler |
| David Haydn-Jones | Mark |
Four friends face the prospect of turning 30 and losing the freedom of their youth. For one, Michael, the transition is especially difficult; although he is in love with Jenna, the mother of his child, his panicked reaction to the onset of adult responsibilities sends him into the arms of another woman .
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