Meg Ryan
Kathleen Kelly
Tom Hanks
Joe Fox
Greg Kinnear
Frank Navasky
Parker Posey
Patricia Eden
Heather Burns
Christina Plutzker
Dave Chappelle
Kevin Jackson
Jean Stapleton
Birdie Conrad
Steve Zahn
George Pappas
Dabney Coleman
Nelson Fox
John Randolph
Schulyer Fox
Hallee Hirsh
Annabelle Fox
Jeffrey Scaperrotta
Matt Fox
Cara Seymour
Gillian Quinn
Katie Finneran
Maureen, the Nanny
Michael Badalucco
Charlie
Deborah Rush
Veronica Cash
Veanne Cox
Miranda Margulies
Bruce Jay Friedman
Vince Mancini
Sara Ramirez
Rose, Zabars Cashier
Howard Spiegel
Henry, Zabars Shopper
Diane Sokolow
Zabars Shopper
Julie Kass
Zabars Shopper
Reiko Aylesworth
Thanksgiving Guest
Katie Sagona
Young Kathleen Kelly
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
Chris Messina
Fox Salesperson
Ronobir Lahiri
Man at Cafe Lalo
André Sogliuzzo
Waiter at 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
Jane Adams
Sydney Anne (uncredited)
Cecelia Antoinette
Restaurant Patron (uncredited)
Elwood Edwards
Online 'You've Got Mail' Voice (voice) (uncredited)
Alfonso Gomez-Rejon
Party Guest (uncredited)
Gideon Jacobs
Young Joe Fox (uncredited)
Brick Mason
Man Letting Joe Fox in (uncredited)
Scott Mullin
Male Runner (uncredited)
Logan Steinhardt
Kid in Bookstore (uncredited)
Anthony Welch
Business Executive (uncredited)