Meg Ryan as Kathleen Kelly

Tom Hanks as Joe Fox

Greg Kinnear as Frank Navasky

Heather Burns as Christina Plutzker

Parker Posey as Patricia Eden

Dave Chappelle as Kevin Jackson

Jean Stapleton as Birdie Conrad

Steve Zahn as George Pappas

Dabney Coleman as Nelson Fox

John Randolph as Schulyer Fox

Hallee Hirsh as Annabelle Fox

Jeffrey Scaperrotta as Matt Fox

Cara Seymour as Gillian Quinn

Katie Finneran as Maureen, the Nanny

Michael Badalucco as Charlie

Deborah Rush as Veronica Cash

Veanne Cox as Miranda Margulies

Bruce Jay Friedman as Vince Mancini

Sara Ramirez as Rose, Zabars Cashier

Howard Spiegel as Henry, Zabars Shopper

Diane Sokolow as Zabars Shopper

Julie Kass as Zabars Shopper

Reiko Aylesworth as Thanksgiving Guest

Katie Sagona as Young Kathleen Kelly

Kathryn Meisle as Cecilia Kelly

Nina Zoie Lam as T.V. Reporter

Maggie Murphy as Theater Patron

Michelle Blakely as Shopper

Meredith White as Shopper

Dianne Dreyer as Shopper

Julie Galdieri as Shopper

Leila Nichols as Shopper

Mary A. Kelly as Fox Books Shopper

Chris Messina as Fox Salesperson

Ronobir Lahiri as Man at Cafe Lalo

André Sogliuzzo as Waiter at Lalo

Peter A. Mian as Capeman

Richard Cohen as Starbucks Customer

Enzo Angileri as Starbucks Customer

Nick Brown as Juggler

Ann Fleuchaus as Sarah Mancini

Neil Bonin as Party Guest

Bill McHugh as Party Guest

Santiago Quinones as Decorator

Lynn Grossman as Yvette Fox

Dolores Sirianni as Mother of Twins

Nicole Bernadette as Florist

Jane Adams as Sydney Anne (uncredited)

Cecelia Antoinette as Restaurant Patron (uncredited)

Elwood Edwards as Online 'You've Got Mail' Voice (voice) (uncredited)

Alfonso Gomez-Rejon as Party Guest (uncredited)

Gideon Jacobs as Young Joe Fox (uncredited)

Brick Mason as Man Letting Joe Fox in (uncredited)

Scott Mullin as Male Runner (uncredited)

Logan Steinhardt as Kid in Bookstore (uncredited)

Anthony Welch as Business Executive (uncredited)