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