Lovestruck Dustin is dating Alexis, his ideal girlfriend, but when she dumps him for coming on too strong, Dustin takes drastic measures to win her back. He asks his best friend Tank to take her on the worst rebound date imaginable - his side job - so that she will come running back to him, and Tank reluctantly agrees. However, Alexis is more than a match for Tank's shock tactics and he begins to really fall for her, leaving him torn between loyalty to Dustin and his growing attraction toward Alexis.
Dane Cook
Tank
Kate Hudson
Alexis
Jason Biggs
Dustin
Alec Baldwin
Professor Turner
Lizzy Caplan
Ami
Diora Baird
Rachel
Taran Killam
Josh
Riki Lindhome
Hilary
Nate Torrence
Craig
Mini Anden
Lizzy
Hilary Pingle
Claire
Malcolm Barrett
Dwalu
Faye Grant
Merrilee
Amanda Brooks
Carly
Richard Snee
Brian
Alberto Bonilla
Pedro
Sally Pressman
Courtney
Kate Albrecht
Laney the Babysitter
Rakefet Abergel
Heavily Pierced Kid
Andrew Lewis Caldwell
Sad Dork
Maureen Keiller
Seamstress
Tom Kemp
Priest
Tony V.
Chef Slava
Jacqui Holland
Kindly Stripper
Andria Blackman
Ms. Barber
Georgia Lyman
Hot Coed
Melina Lizette
Ms. Reiling
Josh Alexander
Burt
Jenny Mollen
Colleen
Eamon Brooks
Random Guy
Cyce Sadsad
Random Guy's Girl
Rob Rota
Lee
Edna Panaggio
Grandmother
Peggy McClellan
Angry Date Throwing Water
Brad Garrett
Irate Customer on Phone (voice) (uncredited)
Susan Garfield
Wedding Guest
Michael O'Toole
Michi Yamana
Community
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