Alex "Hitch" Hitchens

Will Smith

Sara

Eva Mendes

Driver

Michael Colgan

Albert

Kevin James

Allegra Cole

Amber Valletta

Casey Sedgewick

Julie Ann Emery

Max

Adam Arkin

Cressida Baylor

Robinne Lee

Ben

Michael Rapaport

Geoff

Nathan Lee Graham

Vance Munson

Jeffrey Donovan

Mandy

Paula Patton

Mr. O'Brian

Philip Bosco

Tanis

Ato Essandoh

Neil

Kevin Sussman

Mika

Navia Nguyen

Bartender

Darrell Foster

Marla

Amy Hohn

Pete

Matt Malloy

Lisa

Maria Thayer

Reporter

Janet Huege

Kim (uncredited)

Rebecca Mader

Stephanie

Marlyne Barrett

Tom Reda

Jack Hartnett

Casper Andreas

Chip

David Wike

Larry

Frederick B. Owens

Louise

Jenna Stern

Magnus “Maggie” Forester

Austin Lysy

Speed Dating Guy

Adam LeFevre

Alan Arkin

Music Lover Guy

Joe Lo Truglio

Charles Wellington

Ryan Cross

Drugstore Clerk

Beau Sia

Ron

Ptolemy Slocum

Coca Cola Guy (uncredited)

Fran Kranz

Guy Nearby

Kahan James

Eddie

Matt Servitto

Grandma Wellington

Mimi Weddell

Gorgeous Wife

Caprice Benedetti

Kate

Rain Phoenix

Raoul

Maulik Pancholy

Hot Date (uncredited)

Anya Avaeva

Student on Class Trip (uncredited)

Brielle Barbusca

Nebbishy Husband

Tony Travis

Maria

Mercedes López Renard

Ross

Jose Llana

Michelle Deighton

Sous Chef

Niels Koizumi

First Date Woman (uncredited)

Michelle DiBenedetti

Cooking Teacher

Chris Santos

Yoga Student (uncredited)

Alexa Lane

Kurt

Tobias Truvillion

Egon

Jeffrey Carlson

Zak

Henri Binje

Newsguy

Remy K. Selma

Beautiful Yatch Owner (uncredited)

Olivia Weston

Waxer

Mika Nishida

Messenger

Trevor Oswalt

Bar Girl (uncredited)

Valbona Coba

Female Speed Dater (uncredited)

Amy Metroka

Elevator Girl (uncredited)

Joanna Lu

Carol (uncredited)

Ava Lee Scott