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
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 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