John Cusack
Jonathan Trager
Acting
Kate Beckinsale
Sara Thomas
Acting
Jeremy Piven
Dean Kansky
Acting
Bridget Moynahan
Halley Buchanan
Acting
John Corbett
Lars Hammond
Acting
Molly Shannon
Eve
Acting
Eugene Levy
Bloomingdale's Salesman
Acting
Lilli Lavine
Bloomingdale's Stock Girl
Acting
Michael Guarino, Jr.
Customer at Bloomingdale's
Acting
Abdul Alshawish
Customer at Bloomingdale's
Acting
Stephen Bruce
Host at Serendipity
Acting
David Sparrow
Josh's Dad
Acting
Gary Gerbrandt
Josh
Acting
Ann Talman
Bloomingdale's Saleswoman #1
Acting
Crystal Bock
Bloomingdale's Saleswoman #2
Acting
Kate Blumberg
Courtney Kansky
Acting
Ron Payne
Louis Trager
Acting
Marcia Bennett
Mrs. Louis Trager
Acting
Eve Crawford
Mrs. Buchanan
Acting
Victor A. Young
Mr. Buchanan
Acting
Leo Fitzpatrick
Leasing Office Temp
Acting
Evan Neumann
Kenny
Acting
Lucy Gordon
Caroline Mitchell
Acting
Kevin Rice
Kip
Acting
Brenda Logan
Hair Stylist
Acting
James Goodwin
Nick Roberts
Acting
John Ellison Conlee
Artie
Acting
Charles A. Gargano
Announcer At Golf Range
Acting
Arthur Pascuzzi
Golf Instructor
Acting
Mike Benitez
Superintendent
Acting
Christopher James Baker
Lars Band #1
Acting
Neil Claxton
Lars Band #2
Acting
Sandra Caldwell
PR Woman
Acting
Ajay Mehta
Pakistani Cab Driver
Acting
Clark Middleton
Airport Cab Driver
Acting
Marqus Bobesich
Street Vendor
Acting
Kevin Kean Murphy
Man On Street
Acting
Paul Rutledge
Golf Ball Man
Crew
Simon Jutras
Sebastian Mignon
Acting
Pamela Redfern
Flight Attendant
Acting
Aron Tager
Janitor
Acting
Catherine Kuhn
Wedding Coordinator
Acting
Buck Henry
Customer at Bloomingdales (uncredited)
Acting