Will Smith as Hitch

Eva Mendes as Sara

Kevin James as Albert

Amber Valletta as Allegra

Julie Ann Emery as Casey

Adam Arkin as Max

Robinne Lee as Cressida

Nathan Lee Graham as Geoff

Michael Rapaport as Ben

Jeffrey Donovan as Vance

Paula Patton as Mandy

Philip Bosco as Mr. O'Brian

Kevin Sussman as Neil

Navia Nguyen as Mika

Matt Malloy as Pete

Maria Thayer as Lisa

Ato Essandoh as Tanis

Marlyne Barrett as Stephanie

Jack Hartnett as Tom Reda

David Wike as Chip

Frederick B. Owens as Larry

Jenna Stern as Louise

Austin Lysy as Magnus

Adam LeFevre as Speed Dating Guy

Joe Lo Truglio as Music Lover Guy

Ptolemy Slocum as Ron

Kahan James as Guy Nearby

Matt Servitto as Eddie

Amy Hohn as Marla

Mimi Weddell as Grandma Wellington

Maulik Pancholy as Raoul

Caprice Benedetti as Gorgeous Wife

Tony Travis as Nebbishy Husband

Mercedes López Renard as Maria

Jose Llana as Ross

Niels Koizumi as Sous Chef

Chris Santos as Cooking Teacher

Ryan Cross as Charles Wellington

Tobias Truvillion as Kurt

Jeffrey Carlson as Egon

Henri Binje as Zak

Rain Phoenix as Kate

Remy K. Selma as Newsguy

Beau Sia as Drugstore Clerk

Mika Nishida as Waxer

Trevor Oswalt as Messenger

Darrell Foster as Bartender

Fran Kranz as Coca Cola Guy (uncredited)

Anya Avaeva as Hot Date (uncredited)

Brielle Barbusca as Student on Class Trip (uncredited)

Kimberly Cash as Kissing Girl (uncredited)

Valbona Coba as Bar Girl (uncredited)

Michelle DiBenedetti as First Date Woman (uncredited)

Alexa Lane as Yoga Student (uncredited)

Christina Lauren as Bar Girl (uncredited)

Rebecca Mader as Kim (uncredited)

Amy Metroka as Female Speed Dater (uncredited)

Jennifer Pedersen as Bar Girl (uncredited)

Keri Uribe as Sara's Nosey Officemate (uncredited)

Olivia Weston as Beautiful Yatch Owner (uncredited)

Dianne Zaremba as Sara's Co-Worker (uncredited)

Joanna Lu as Elevator Girl (uncredited)

Ava Lee Scott as Carol (uncredited)