Will Smith

Character: Hitch

Eva Mendes

Character: Sara

Kevin James

Character: Albert

Amber Valletta

Character: Allegra

Julie Ann Emery

Character: Casey

Adam Arkin

Character: Max

Robinne Lee

Character: Cressida

Nathan Lee Graham

Character: Geoff

Michael Rapaport

Character: Ben

Jeffrey Donovan

Character: Vance

Paula Patton

Character: Mandy

Philip Bosco

Character: Mr. O'Brian

Kevin Sussman

Character: Neil

Navia Nguyen

Character: Mika

Matt Malloy

Character: Pete

Maria Thayer

Character: Lisa

Ato Essandoh

Character: Tanis

Marlyne Barrett

Character: Stephanie

Jack Hartnett

Character: Tom Reda

David Wike

Character: Chip

Frederick B. Owens

Character: Larry

Jenna Stern

Character: Louise

Austin Lysy

Character: Magnus

Adam LeFevre

Character: Speed Dating Guy

Joe Lo Truglio

Character: Music Lover Guy

Ptolemy Slocum

Character: Ron

Kahan James

Character: Guy Nearby

Matt Servitto

Character: Eddie

Amy Hohn

Character: Marla

Mimi Weddell

Character: Grandma Wellington

Maulik Pancholy

Character: Raoul

Caprice Benedetti

Character: Gorgeous Wife

Tony Travis

Character: Nebbishy Husband

Mercedes López Renard

Character: Maria

Jose Llana

Character: Ross

Niels Koizumi

Character: Sous Chef

Chris Santos

Character: Cooking Teacher

Ryan Cross

Character: Charles Wellington

Tobias Truvillion

Character: Kurt

Jeffrey Carlson

Character: Egon

Henri Binje

Character: Zak

Rain Phoenix

Character: Kate

Remy K. Selma

Character: Newsguy

Beau Sia

Character: Drugstore Clerk

Mika Nishida

Character: Waxer

Trevor Oswalt

Character: Messenger

Darrell Foster

Character: Bartender

Fran Kranz

Character: Coca Cola Guy (uncredited)

Anya Avaeva

Character: Hot Date (uncredited)

Brielle Barbusca

Character: Student on Class Trip (uncredited)

Kimberly Cash

Character: Kissing Girl (uncredited)

Valbona Coba

Character: Bar Girl (uncredited)

Michelle DiBenedetti

Character: First Date Woman (uncredited)

Alexa Lane

Character: Yoga Student (uncredited)

Christina Lauren

Character: Bar Girl (uncredited)

Rebecca Mader

Character: Kim (uncredited)

Amy Metroka

Character: Female Speed Dater (uncredited)

Jennifer Pedersen

Character: Bar Girl (uncredited)

Keri Uribe

Character: Sara's Nosey Officemate (uncredited)

Olivia Weston

Character: Beautiful Yatch Owner (uncredited)

Dianne Zaremba

Character: Sara's Co-Worker (uncredited)

Joanna Lu

Character: Elevator Girl (uncredited)

Ava Lee Scott

Character: Carol (uncredited)