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