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