| Freddie Prinze Jr. | Ryan Williams |
| Claire Forlani | Jennifer |
| Jason Biggs | Hunter (Steve) |
| Amanda Detmer | Amy |
| Heather Donahue | Megan |
| Alyson Hannigan | Beth |
| Raquel Beaudine | Young Jennifer Burrows |
| Brendon Ryan Barrett | Young Ryan |
| Lisa Eichhorn | Shuttle Passenger |
| Monica Arnold | Katie |
Two longtime friends, each with a string of failed romances, wonder if they should date each other.
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