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