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Cast (23)
Freddie Prinze Jr.
as Alfred 'Al' Connelly
Julia Stiles
as Imogen
Selma Blair
as Cyrus
Shawn Hatosy
as Eddie Hicks
Zak Orth
as Monk Jablonski
Ashton Kutcher
as Jim Morrison
Rosario Dawson
as Lana
Henry Winkler
as Chef Ray
Lucie Arnaz
as Judy Connelly
Lauren German
as Lovestruck Woman
Zay Harding
as Lovestruck Man
Mark Blum
as The Interviewer
Amanda Barfield
as Faith Keenan
Chloe Hunter
as Megan Brodski
G.G
Granger Green
as Haley Heller
J.R
Jed Rhein
as Gabe Stiano
Bradley Pierce
as Ricky James
Alexia Landeau
as Cousin Maeva
Adam Carolla
as 'The Man Show' Host
Jimmy Kimmel
as 'The Man Show' Host
Caroline Ambrose
as Al's First Kiss
Joanna Adler
as Piercing Woman
Frank Wood
as Doctor
