Will Smith

Hitch

Eva Mendes

Sara

Kevin James

Albert

Amber Valletta

Allegra

Julie Ann Emery

Casey

Adam Arkin

Max

Robinne Lee

Cressida

Nathan Lee Graham

Geoff

Michael Rapaport

Ben

Jeffrey Donovan

Vance

Paula Patton

Mandy

Philip Bosco

Mr. O'Brian

Kevin Sussman

Neil

Navia Nguyen

Mika

Matt Malloy

Pete

Maria Thayer

Lisa

Ato Essandoh

Tanis

Marlyne Barrett

Stephanie

Jack Hartnett

Tom Reda

David Wike

Chip

Frederick B. Owens

Larry

Jenna Stern

Louise

Austin Lysy

Magnus

Adam LeFevre

Speed Dating Guy

Joe Lo Truglio

Music Lover Guy

Ptolemy Slocum

Ron

Kahan James

Guy Nearby

Matt Servitto

Eddie

Amy Hohn

Marla

Mimi Weddell

Grandma Wellington

Maulik Pancholy

Raoul

Caprice Benedetti

Gorgeous Wife

Tony Travis

Nebbishy Husband

Mercedes López Renard

Maria

Niels Koizumi

Sous Chef

Tobias Truvillion

Kurt

Henri Binje

Zak

Rain Phoenix

Kate

Beau Sia

Drugstore Clerk

Darrell Foster

Bartender

Fran Kranz

Coca Cola Guy (uncredited)

Anya Avaeva

Hot Date (uncredited)

Brielle Barbusca

Student on Class Trip (uncredited)

Michelle DiBenedetti

First Date Woman (uncredited)

Rebecca Mader

Kim (uncredited)