John Cusack

Jonathan Trager

Eugene Levy

Bloomingdale's Salesman

Jeremy Piven

Dean Kansky

Molly Shannon

Eve

Amy Slotnick

Executive Producer

Bridget Moynahan

Halley Buchanan

Eve Crawford

Mrs. Buchanan

John Corbett

Lars Hammond

Julie Goldstein

Executive Producer

Marcia Bennett

Mrs. Louis Trager

Victor A. Young

Mr. Buchanan

Kate Beckinsale

Sara Thomas

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

Leo Fitzpatrick

Leasing Office Temp

Evan Neumann

Kenny

Lucy Gordon

Caroline Mitchell

Kevin Rice

Kip

Peter Chelsom

Director

Robert L. Levy

Executive Producer

Bob Osher

Executive Producer

Marc Klein

Writer