Tom Hanks .... Joe Fox aka NY152
Meg Ryan .... Kathleen Kelly aka Shopgirl
Greg Kinnear .... Frank Navasky
Parker Posey .... Patricia Eden
Jean Stapleton .... Birdie Conrad
Steve Zahn .... George Pappas
Heather Burns .... Christina Plutzker
David Chappelle .... Kevin Jackson (as Dave Chappelle)
Dabney Coleman .... Nelson Fox
John Randolph .... Schuyler Fox
Deborah Rush .... Veronica Grant
Hallee Hirsh .... Annabelle Fox
Jeffrey Scaperrotta .... Matthew 'Matt' Fox
Cara Seymour .... Gillian Quinn
Katie Finneran .... Maureen, the Nanny
Michael Badalucco .... Charlie
Veanne Cox .... Miranda Margulies
Bruce Jay Friedman .... Vince Mancini
Sara Ramirez .... Rose, Zabar's Cashier
Howard Spiegel .... Henry, Zabar's Shopper
Diane Sokolow .... Zabar's Shopper
Julie Kass .... Zabar's Shopper
Reiko Aylesworth .... Thanksgiving Guest
Kathryn Meisle .... Cecilia Kelly
Nina Zoie Lam .... T.V. Reporter
Maggie Murphy .... Theater Patron
Michelle Blakely .... Shopper
Meredith White .... Shopper
Dianne Dreyer .... Shopper
Julie Galdieri .... Shopper
Leila Nichols .... Shopper
Mary A. Kelly .... Fox Books Shopper (as Mary Kelly)
Chris Messina .... Fox Salesperson
Ronobir Lahiri .... Man at Cafe Lalo
André Sogliuzzo .... Waiter at Cafe Lalo
Peter A. Mian .... Capeman
Richard Cohen .... Starbucks Customer
Enzo Angileri .... Starbucks Customer
Nick Brown .... Juggler
Ann Fleuchaus .... Sarah Mancini
Neil Bonin .... Party Guest
Bill McHugh .... Party Guest
Santiago Quinones .... Decorator
Lynn Grossman .... Yvette Fox
Dolores Sirianni .... Mother of Twins
Nicole Bernadette .... Florist
Carole King .... Singer: 'Anyone At All' (voice)
Jane Adams .... Sydney Anne (uncredited)
Elwood Edwards .... Online 'You've Got Mail' Voice (voice) (uncredited)
Alfonso Gomez-Rejon .... Party guest (uncredited)
Brick Mason .... Woman Letting Joe Fox in (uncredited)
Katie Sagona .... Young Kathleen Kelly (flashback sequence) (uncredited)

The owner of a large bookstore chain starts putting the owner of a small local bookstore out of business. Meanwhile they have been corresponding over the internet without knowing who either of them are. They can't stand each other in person but over the internet they are very attracted. He finds out who she is but she doesn't know. He starts to like her more but she still hates him. He has to fix it.

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