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Kissing a Fool (1998)
R
93 min | Comedy, Romance

Writer Jay and womanizing sportscaster Max have been friends since birth. Jay introduces his editor Samantha to Max and they hit it off. Max wants Jay to try to seduce Sam to test her before their wedding.
Read more: Plot summary
Director
Writers
James Frey (story) (screenplay) | Doug Ellin (screenplay)
Cinematographer
Casting Director
Production Designer
Charles William Breen (as Charles Breen)
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Release date
Feb 27, 1998 (United States)

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Cast

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30 cast members
Name STARmeter Known for
David Schwimmer
Max Abbitt Max Abbitt   See fewer
Top 5000
Jason Lee
Jay Murphy Jay Murphy   See fewer
Top 5000
Mili Avital
Samantha Andrews Samantha Andrews   See fewer
Top 5000
Top 5000
Vanessa Angel
Natasha Natasha   See fewer
Top 5000
Top 5000
Frank Medrano
Cliff Randal Cliff Randal   See fewer
Members only
Bitty Schram
Vicki Pelam Vicki Pelam   See fewer
Top 5000
Judy Greer
Andrea Andrea   See fewer
Top 5000
Ron Beattie
Priest Priest   See fewer
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Doug Ellin
Bartender / Springer Guest Bartender / Springer Guest   See fewer
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Tag Mendillo
Wedding Guest at Bar / Springer Guest Wedding Guest at Bar / Springer Guest   See fewer
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Justine Bentley
Beautiful Woman at Bar Beautiful Woman at Bar   See fewer
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Liza Cruzat
Dara's Friend #1 Dara's Friend #1   See fewer
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Jessica Mills
Dara's Friend #2 Dara's Friend #2   See fewer
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Sammy Sosa
Sammy Sosa Sammy Sosa   See fewer
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Jerry Springer
Jerry Springer Jerry Springer   See fewer
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Mike Squire
Spanish Man in Bed Spanish Man in Bed   See fewer
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Marco Siviero
French Man in Bed French Man in Bed   See fewer
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Steve Seagren
Heckler Heckler   See fewer
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Philip Rayburn Smith
Fan on the Street (as Philip R. Smith) Fan on the Street (as Philip R. Smith)   See fewer
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Jayson Fate
Rudolpho Rudolpho   See fewer
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Ross Bon
Blue Kings Lead Singer Blue Kings Lead Singer   See fewer
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Members only
Andy-John
Dining Host (uncredited) Dining Host (uncredited)   See fewer
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Charles William Breen
Jay's Agent (uncredited) Jay's Agent (uncredited)   See fewer
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Christopher Free
Springer Audience Member (uncredited) Springer Audience Member (uncredited)   See fewer
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Amy McLott
Beautiful Woman on Rollerblades (uncredited) Beautiful Woman on Rollerblades (uncredited)   See fewer
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Sean Riggs
Bar Patron (uncredited) Bar Patron (uncredited)   See fewer
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Shannon Watson
Timmy (uncredited) Timmy (uncredited)   See fewer
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Ratings Breakdown

5.6 / 10 | 5,241 votes