John Cusack character Jonathan Trager
Kate Beckinsale character Sara Thomas
Jeremy Piven character Dean Kansky
Bridget Moynahan character Halley Buchanan
Eugene Levy character Bloomingdale's Salesman
Lilli Lavine character Bloomingdale's Stock Girl
Michael Guarino Jr. character Customer at Bloomingdale's
Abdul Alshawish character Customer at Bloomingdale's
Stephen Bruce character Host at Serendipity
David Sparrow character Josh's Dad
Ann Talman character Bloomingdale's Saleswoman #1
Crystal Bock character Bloomingdale's Saleswoman #2
Kate Blumberg character Courtney Kansky
Gary Gerbrandt character Josh
Ron Payne character Louis Trager
Marcia Bennett character Mrs. Louis Trager
Eve Crawford character Mrs. Buchanan
Victor A. Young character Mr. Buchanan
Molly Shannon character Eve
Leo Fitzpatrick character Leasing Office Temp
Evan Neumann character Kenny
John Corbett character Lars Hammond
Lucy Gordon character Caroline Mitchell
Kevin Rice character Kip
Brenda Logan character Hair Stylist
James Goodwin character Nick Roberts
John Ellison Conlee character Artie
Charles A. Gargano character Announcer At Golf Range
Arthur Pascuzzi character Golf Instructor
Mike Benitez character Superintendent
Christopher James Baker character Lars Band #1
Neil Claxton character Lars Band #2
Sandra Caldwell character PR Woman
Ajay Mehta character Pakistani Cab Driver
Clark Middleton character Airport Cab Driver
Marqus Bobesich character Street Vendor
Kevin Kean Murphy character Man On Street
Paul Rutledge character Golf Ball Man
Simon Jutras character Sebastian Mignon
Pamela Redfern character Flight Attendant
