John Oates
— Himself
Thomas Lyons
— Dave Bertman
Craig Shoemaker
— Narrator
Heather Sossaman
— Gina Marie
Chris Dollard
— Gizmo Gouda
Kelly Perine
— Skip
Michelle Stafford
— Ex-Wife Jessica
Dale Midkiff
— Doug
Sharon Amos
— Stephanie
Brooke Hasalton
— Debater Judith
Domenick Dicce
— Nervous Dater
Steve Hytner
— Hack Murphy
Alex Rodruquez
— Matt - Stoner #2
Tim Bagley
— Rusty Polten
Rich Hardisty
— Debater Rich (Segment "Reunion Party")