John Cusack as Jonathan Trager

Kate Beckinsale as Sara Thomas

Jeremy Piven as Dean Kansky

Bridget Moynahan as Halley Buchanan

John Corbett as Lars Hammond

Molly Shannon as Eve

Eugene Levy as Bloomingdale's Salesman

Lilli Lavine as Bloomingdale's Stock Girl

Michael Guarino, Jr. as Customer at Bloomingdale's

Abdul Alshawish as Customer at Bloomingdale's

Stephen Bruce as Host at Serendipity

David Sparrow as Josh's Dad

Gary Gerbrandt as Josh

Ann Talman as Bloomingdale's Saleswoman #1

Crystal Bock as Bloomingdale's Saleswoman #2

Kate Blumberg as Courtney Kansky

Ron Payne as Louis Trager

Marcia Bennett as Mrs. Louis Trager

Eve Crawford as Mrs. Buchanan

Victor A. Young as Mr. Buchanan

Leo Fitzpatrick as Leasing Office Temp

Evan Neumann as Kenny

Lucy Gordon as Caroline Mitchell

Kevin Rice as Kip

Brenda Logan as Hair Stylist

James Goodwin as Nick Roberts

John Ellison Conlee as Artie

Charles A. Gargano as Announcer At Golf Range

Arthur Pascuzzi as Golf Instructor

Mike Benitez as Superintendent

Christopher James Baker as Lars Band #1

Neil Claxton as Lars Band #2

Sandra Caldwell as PR Woman

Ajay Mehta as Pakistani Cab Driver

Clark Middleton as Airport Cab Driver

Marqus Bobesich as Street Vendor

Kevin Kean Murphy as Man On Street

Paul Rutledge as Golf Ball Man

Simon Jutras as Sebastian Mignon

Pamela Redfern as Flight Attendant

Aron Tager as Janitor

Catherine Kuhn as Wedding Coordinator

Buck Henry as Customer at Bloomingdales (uncredited)