Greg Kinnear
Frank Navasky
Heather Burns
Christina Plutzker
Parker Posey
Patricia Eden
Dave Chappelle
Kevin Jackson
Jean Stapleton
Birdie Conrad
John Randolph
Schulyer Fox
Hallee Hirsh
Annabelle Fox
Jeffrey Scaperrotta
Matt Fox
Cara Seymour
Gillian Quinn
Katie Finneran
Maureen, the Nanny
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
Reiko Aylesworth
Thanksgiving Guest
Katie Sagona
Young Kathleen Kelly
Kathryn Meisle
Cecilia Kelly
Nina Zoie Lam
T.V. Reporter
Maggie Murphy
Theater Patron
Mary A. Kelly
Fox Books Shopper
Chris Messina
Fox Salesperson
Ronobir Lahiri
Man at Cafe Lalo
André Sogliuzzo
Waiter at Lalo
Richard Cohen
Starbucks Customer
Enzo Angileri
Starbucks Customer
Ann Fleuchaus
Sarah Mancini
Santiago Quinones
Decorator
Dolores Sirianni
Mother of Twins
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)