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