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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)