Jerry O'Connell as David Collins

Bridgette Wilson-Sampras as Sarah

Ryan Reynolds as Mike Hanson

Bill Bellamy as Jonesy

Alyssa Milano as Amy

Jon Tenney as Andrew Hahn

Annabeth Gish as Nicole

Ron Livingston as Tyler Bellows

Erinn Bartlett as Julie Madison

Scarlett Chorvat as Katie Madison

Jolie Jenkins as Amber

John O'Hurley as Tim 'Timbo' Chadway

Alicia Rickter as Laura

Brian Beacock as Alex

Heather Morgan as Waitress

David DeLuise as Fratguy

Nina Petronzio as Cynthia

Fiona Loewi as Susan

Nipper Knapp as Host

S.A. Griffin as Stanley

Ruthanna Hopper as Lisa

C.C. Boyce as Nikki

Cie Allman as Nancy (uncredited)