Jonathan Trager

John Cusack

Sara Thomas

Kate Beckinsale

Dean Kansky

Jeremy Piven

Eve

Molly Shannon

Halley Buchanan

Bridget Moynahan

Lars Hammond

John Corbett

Bloomingdale's Salesman

Eugene Levy

Mrs. Trager

Marcia Bennett

Caroline Mitchell

Lucy Gordon

Courtney

Kate Blumberg

Bloomingdale's Stock Girl

Lilli Lavine

Mrs. Buchanan

Eve Crawford

Kenny

Evan Neuman

Superintendent

Mike Benitez

Customer at Bloomingdale's

Michael Guarino Jr.

Flight Attendant

Pamela Redfern

Glove Shopper (uncredited)

Buck Henry

Customer at Bloomingdale's

Abdul Alshawish

Hair Stylist

Brenda Logan

Host at Serendipity

Stephen Bruce

Kip Mitchell

Kevin Rice

Josh's Dad

David Sparrow

Hippie Woman

Colleen Williams

Josh

Gary Gerbrandt

Bloomingdale's Saleswoman #1

Ann Talman

Janitor

Aron Tager

Bloomingdale's Saleswoman #2

Crystal Bock

Lars' Band Member No. 1

Christopher Baker

Lars' Band Member No. 2

Neil Claxton

Priest

Murray McRae

Louis Trager

Ron Payne

Mr. Buchanan

Victor A. Young

Leasing Office Temp

Leo Fitzpatrick

Artie

John Ellison Conlee

Mr. Buchanan

Victor Young

Nick Roberts

James Goodwin

Nick Roberts

Jamie Goodwin

Announcer At Golf Range

Charles A. Gargano

Pakistani Driver

Ajay Mehta

PR Woman

Sandra Caldwell

Golf Instructor

Arthur Pascuzzi

Rastafarian

Reggi Wyns

Ryan

T. Scott Cunningham

Sara Lawson

Jessica Kelly

Sebastain

Simon Jutras

Street Vendor

Marqus Bobesich

Waitress at Serendipity

Catherine Hernandez

Airport Cab Driver

Clark Middleton

Wedding Coordinator

Catherine Kuhn

Man On Street

Kevin Kean Murphy

Golf Ball Man

Paul Rutledge

Check-in Clerk

Conrad Bergschneider

Amita Balla

Tony Kaan

Dianne Wiest

Angela Lansbury

Artie

John Conlee

Director

Peter Chelsom