

08/03/1997
Three best friends mess up their already flagging love lives with an ill-fated bet. They each put two thousand dollars in a bank account, with the winner being the one who can not only get a girlfriend, but also live with her for three months. Nick decides to hoodwink his two friends by faking a relationship with an old girlfriend from college, while Al proceeds to embark on a series of the worst dates imaginable, and Les finds himself getting deeply involved with an alluring but mysterious woman who may or may not be married to a mobster. Hilarious antics lead to an unexpected outcome guaranteed to surprise.

Grant Shaud
as Les

Will Ferrell
as Al

Anthony Palermo
as Nick

Starr Andreeff
as Misty

Pamela Gien
as Celia

Rebeca Arthur
as Sharon

Nia Vardalos
as Iris

Maureen Teefy
as Teri

Holly Long
as Brunette

Lisa Wilcox
as Judy

Kelly Coleman
as Bag Woman

Rebecca Wackler
as Dale

Tia Riebling
as Monica

Tangie Ambrose
as Grace

Gloria Perez
as Helena

Tricia Leigh Fisher
as Amanda

Suzy Nakamura
as Cassie

Stacy Edwards
as Jennifer

Jennifer Barker
as Angie

James Intveld
as Jimmy and the Gigolos

Edward Perez
as Jimmy and the Gigolos

Denny Croy
as Jimmy and the Gigolos

Michael Rose
as Jimmy and the Gigolos

Richard Green
as Jimmy and the Gigolos

Kenny Sira
as Jimmy and the Gigolos

Dax Griffin
as Jimmy and the Gigolos

Jeff Turmes
as Jimmy and the Gigolos
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