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Meg RyanKathleen Kelly
Tom HanksJoe Fox
Greg KinnearFrank Navasky
Heather BurnsChristina Plutzker
Parker PoseyPatricia Eden
Dave ChappelleKevin Jackson
Jean StapletonBirdie Conrad
Steve ZahnGeorge Pappas
Dabney ColemanNelson Fox
John RandolphSchulyer Fox
Hallee HirshAnnabelle Fox
Jeffrey ScaperrottaMatt Fox
Cara SeymourGillian Quinn
Katie FinneranMaureen, the Nanny
Michael BadaluccoCharlie
Deborah RushVeronica Cash
Veanne CoxMiranda Margulies
Bruce Jay FriedmanVince Mancini
Sara RamirezRose, Zabars Cashier- Howard SpiegelHenry, Zabars Shopper
Diane SokolowZabars Shopper- Julie KassZabars Shopper
Reiko AylesworthThanksgiving Guest
Katie SagonaYoung Kathleen Kelly
Kathryn MeisleCecilia Kelly- Nina Zoie LamT.V. Reporter
- Maggie MurphyTheater Patron
- Michelle BlakelyShopper
- Meredith WhiteShopper
- Dianne DreyerShopper
Julie GaldieriShopper- Leila NicholsShopper
Mary A. KellyFox Books Shopper
Chris MessinaFox Salesperson
Ronobir LahiriMan at Cafe Lalo
André SogliuzzoWaiter at Lalo- Peter A. MianCapeman
- Richard CohenStarbucks Customer
- Enzo AngileriStarbucks Customer
- Nick BrownJuggler
- Ann FleuchausSarah Mancini
- Neil BoninParty Guest
Bill McHughParty Guest- Santiago QuinonesDecorator
- Lynn GrossmanYvette Fox
- Dolores SirianniMother of Twins
- Nicole BernadetteFlorist
Jane AdamsSydney Anne (uncredited)
Cecelia AntoinetteRestaurant Patron (uncredited)- Elwood EdwardsOnline 'You've Got Mail' Voice (voice) (uncredited)
Alfonso Gomez-RejonParty Guest (uncredited)
Gideon JacobsYoung Joe Fox (uncredited)- Brick MasonMan Letting Joe Fox in (uncredited)
- Scott MullinMale Runner (uncredited)
- Logan SteinhardtKid in Bookstore (uncredited)
- Anthony WelchBusiness Executive (uncredited)