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- Claire Forlani as Jennifer Burrows
- Freddie Prinze, Jr. as Ryan Walker
- Jason Biggs as Hunter / Steve
- Amanda Detmer as Amy
- Heather Donahue as Megan
- Alyson Hannigan as Betty
- Brendon Ryan Barrett as Young Ryan Walker
- Raquel Beaudene as Young Jennifer Burrows
- David Smigelski as Homecoming King
- Blake Shields as Homecoming Knight
- Gay Thomas as N.Y. Flight Attendant
- Renate Verbaan as Farting Super Model