Will Smith

Alex 'Hitch' Hitchens

Eva Mendes

Sara Melas

Kevin James

Albert Brennaman

Amber Valletta

Allegra Cole

Julie Ann Emery

Casey Sedgewick

Adam Arkin

Max

Robinne Lee

Cressida Baylor

Nathan Lee Graham

Geoff

Michael Rapaport

Ben

Jeffrey Donovan

Vance Munson

Paula Patton

Mandy

Philip Bosco

Mr. O'Brian

Kevin Sussman

Neil

Navia Nguyen

Mika

Matt Malloy

Pete

Maria Thayer

Lisa

Ato Essandoh

Tanis

Marlyne Barrett

Stephanie

Jack Hartnett

Tom Reda

David Wike

Chip

Frederick B. Owens

Larry

Jenna Stern

Louise

Austin Lysy

Magnus “Maggie” Forester

Adam LeFevre

Speed Dating Guy

Joe Lo Truglio

Music Lover Guy

Ryan Cross

Charles Wellington

Beau Sia

Drugstore Clerk

Fran Kranz

Coca Cola Guy (uncredited)

Amy Hohn

Marla

Mimi Weddell

Grandma Wellington

Caprice Benedetti

Gorgeous Wife

Rain Phoenix

Kate

Anya Avaeva

Hot Date

Brielle Barbusca

Student on Class Trip

Kimberly Cash

Kissing Girl

Valbona Coba

Bar Girl

Michelle Carlsen

Michelle DiBenedetti

First Date Woman

Alexa Lane

Yoga Student

Christina Lauren

Bar Girl

Rebecca Mader

Kim

Amy Metroka

Female Speed Dater

Maria Nomi

Club Girl

Jennifer Pedersen

Bar Girl

Keri Uribe

Sara's Nosey Officemate

Olivia Weston

Beautiful Yatch Owner

Dianne Zaremba

Sara's Co-Worker

Joanna Lu

Elevator Girl (uncredited)

Mercedes Renard

Maria

Tony Travis

Tony

Ptolemy Slocum

Ron