Will Smith

Alex 'Hitch' Hitchens

Acting

Eva Mendes

Sara Melas

Acting

Kevin James

Albert Brennaman

Acting

Amber Valletta

Allegra Cole

Acting

Julie Ann Emery

Casey Sedgewick

Acting

Adam Arkin

Max

Acting

Robinne Lee

Cressida Baylor

Acting

Nathan Lee Graham

Geoff

Acting

Michael Rapaport

Ben

Acting

Jeffrey Donovan

Vance Munson

Acting

Paula Patton

Mandy

Acting

Philip Bosco

Mr. O'Brian

Acting

Kevin Sussman

Neil

Acting

Navia Nguyen

Mika

Acting

Matt Malloy

Pete

Acting

Maria Thayer

Lisa

Acting

Ato Essandoh

Tanis

Acting

Marlyne Barrett

Stephanie

Acting

Jack Hartnett

Tom Reda

Acting

David Wike

Chip

Writing

Frederick B. Owens

Larry

Acting

Jenna Stern

Louise

Acting

Austin Lysy

Magnus “Maggie” Forester

Acting

Adam LeFevre

Speed Dating Guy

Acting

Joe Lo Truglio

Music Lover Guy

Acting

Ryan Cross

Charles Wellington

Acting

Beau Sia

Drugstore Clerk

Acting

Fran Kranz

Coca Cola Guy (uncredited)

Acting

Amy Hohn

Marla

Acting

Mimi Weddell

Grandma Wellington

Acting

Caprice Benedetti

Gorgeous Wife

Acting

Rain Phoenix

Kate

Acting

Anya Avaeva

Hot Date

Acting

Brielle Barbusca

Student on Class Trip

Acting

Kimberly Cash

Kissing Girl

Acting

Valbona Coba

Bar Girl

Acting

Michelle Carlsen

Acting

Michelle DiBenedetti

First Date Woman

Acting

Alexa Lane

Yoga Student

Acting

Christina Lauren

Bar Girl

Acting

Rebecca Mader

Kim

Acting

Amy Metroka

Female Speed Dater

Acting

Maria Nomi

Club Girl

Acting

Jennifer Pedersen

Bar Girl

Acting

Keri Uribe

Sara's Nosey Officemate

Acting

Olivia Weston

Beautiful Yatch Owner

Acting

Dianne Zaremba

Sara's Co-Worker

Acting

Joanna Lu

Elevator Girl (uncredited)

Production

Mercedes Renard

Maria

Acting

Tony Travis

Tony

Acting

Ptolemy Slocum

Ron

Acting