John Cusack
Jonathan Trager
Kate Beckinsale
Sara Thomas
Molly Shannon
Eve
Jeremy Piven
Dean Kansky
John Corbett
Lars Hammond
Bridget Moynahan
Halley Buchanan
Eugene Levy
Bloomingdale's Salesman
Marcia Bennett
Mrs. Louis Trager
Eve Crawford
Mrs. Buchanan
Leo Fitzpatrick
Leasing Office Temp
Lucy Gordon
Caroline Mitchell
Lilli Lavine
Bloomingdale's Stock Girl
Michael Guarino, Jr.
Customer at Bloomingdale's
Abdul Alshawish
Customer at Bloomingdale's
Stephen Bruce
Host at Serendipity
David Sparrow
Josh's Dad
Ann Talman
Bloomingdale's Saleswoman #1
Crystal Bock
Bloomingdale's Saleswoman #2
Gary Gerbrandt
Josh
Kate Blumberg
Courtney Kansky
Ron Payne
Louis Trager
Victor A. Young
Mr. Buchanan
Reggi Wyns
Rastafarian
Evan Neumann
Kenny
Kevin Rice
Kip
James Goodwin
Nick Roberts
John Ellison Conlee
Artie
Charles A. Gargano
Announcer At Golf Range
Jessica Kelly
Sara Lawson
Arthur Pascuzzi
Golf Instructor
Brenda Logan
Hair Stylist
Thomas "Bravo" Roughan
Bicycle Messenger
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
Paul Rutledge
Golf Ball Man
Simon Jutras
Sebastian Mignon
Pamela Redfern
Flight Attendant
Aron Tager
Janitor
Catherine Kuhn
Wedding Coordinator
Buck Henry
Customer at Bloomingdales (uncredited)
T. Scott Cunningham
Ryan
Colleen Williams
Hippie Woman
Sheldon Krahn
Waiter at Serendipity
Murray McRae
Priest
David Ramsden
Wedding Florist