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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)