John Cusack
Jonathan Trager
Kate Beckinsale
Sara Thomas
Bridget Moynahan
Halley Buchanan
Eugene Levy
Bloomingdale's Salesman
Lilli Lavine
Bloomingdale's Stock Girl
Michael Guarino, Jr.
Customer at Bloomingdale's
Abdul Alshawish
Customer at Bloomingdale's
Stephen Bruce
Host at Serendipity
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
Lucy Gordon
Caroline Mitchell
James Goodwin
Nick Roberts
Charles A. Gargano
Announcer At Golf Range
Arthur Pascuzzi
Golf Instructor
Mike Benitez
Superintendent
Christopher James Baker
Lars Band #1
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
Catherine Kuhn
Wedding Coordinator
Buck Henry
Customer at Bloomingdales (uncredited)