Will Smith as Alex 'Hitch' Hitchens

Eva Mendes as Sara Melas

Kevin James as Albert Brennaman

Amber Valletta as Allegra Cole

Julie Ann Emery as Casey Sedgewick

Adam Arkin as Max

Robinne Lee as Cressida Baylor

Nathan Lee Graham as Geoff

Michael Rapaport as Ben

Jeffrey Donovan as Vance Munson

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 “Maggie” Forester

Adam LeFevre as Speed Dating Guy

Joe Lo Truglio as Music Lover Guy

Ryan Cross as Charles Wellington

Beau Sia as Drugstore Clerk

Fran Kranz as Coca Cola Guy (uncredited)

Amy Hohn as Marla

Mimi Weddell as Grandma Wellington

Caprice Benedetti as Gorgeous Wife

Rain Phoenix as Kate

Anya Avaeva as Hot Date

Brielle Barbusca as Student on Class Trip

Kimberly Cash as Kissing Girl

Valbona Coba as Bar Girl

Michelle Carlsen as

Michelle DiBenedetti as First Date Woman

Alexa Lane as Yoga Student

Christina Lauren as Bar Girl

Rebecca Mader as Kim

Amy Metroka as Female Speed Dater

Maria Nomi as Club Girl

Jennifer Pedersen as Bar Girl

Keri Uribe as Sara's Nosey Officemate

Olivia Weston as Beautiful Yatch Owner

Dianne Zaremba as Sara's Co-Worker

Joanna Lu as Elevator Girl (uncredited)

Mercedes Renard as Maria

Tony Travis as Tony

Ptolemy Slocum as Ron