David seriously fancies smart, rich Carrie as soon as he first offends her in a Boston bar. They run into each other again and though she still finds him appalling, David manages to change her mind.
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Arye Gross as David Crown
Courteney Cox as Carrie Davenport
Kevin Pollak as Eli
Julie Brown as Zoe
Mitchell Ryan as Kenneth Davenport
Mitzi McCall as Freida Crown
B.J. Ward as Giselle Davenport
Philip Bruns as Irv Crown
Jack Carter as Rabbi
Tess Foltyn as Hanna
David DeCastro as Beer Vendor
Donald Brown as Crackerjack Vendor
Aaron Lustig as Movie Bully
Connie Sawyer as Waitress from Hell
Steven Brill as George / French TV Announcer
Davis Guggenheim as Pitcher
Craig Alan Edwards as 1st Baseman
Rob Youngblood as Adam
John DeMita as Chipper
Lisa Waltz as Lizbeth
Kimberlin Brown as Leeza
Kevin West as Tour Guide
Justin Shenkarow as Buddy
Mindy Mittleman as Cindy
Jensen Daggett as Cheerleader
Amanda Foreman as Waitress
Kimber Sissons as Tracy
Larry Poindexter as Carrie's Date
Frank Birney as Priest
Johnny Most as Basketball Announcer
Carrie "CeCe" Cline as Teenage Sunbather (uncredited)