Freddie Prinze Jr.
Jack
Jack's lavish life as a NYC advertising exec collides with Jill's fiery idealism. Opposites attract, but Jill soon violates Rule 1 of Jack's relationship manifesto: "Be Honest."
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Freddie Prinze Jr.
Jack
Taryn Manning
Jill
Peter Stebbings
George
Ingrid Doucet
Sally
Vanessa Parise
Lucy
Lisa Davis
Amberly
Darrin Brown
T-Bone
Claudia Besso
Melony
Krista Sutton
Emily
Julian Richings
Mr. Smith
Ethan Penner
Wyatt
Hannah Lochner
Holly
Kelly Rowan
Kate
Charles Martin Smith
Carlin
Chick Roberts
Mr Bradley
Joan Gregson
Mrs Bradley
Joe Pingue
Casting Director
Robin Dunne
Gary
Robin Dunne
Ignatius the Philosophical Clown
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