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

Michael Guarino, Jr.
Customer at Bloomingdale's

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

Ron Payne
Louis Trager

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

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)