Joaquin Phoenix
Theodore
Acting
Scarlett Johansson
Samantha (voice)
Acting
Lynn Adrianna
Letter Writer #1
Acting
Lisa Renee Pitts
Letter Writer #2
Acting
Gabe Gomez
Letter Writer #3
Acting
Chris Pratt
Paul
Acting
Artt Butler
Text Voice (voice)
Acting
May Lindstrom
Sexy Pregnant TV Star
Acting
Rooney Mara
Catherine
Acting
Bill Hader
Chat Room Friend #2 (voice)
Acting
Kristen Wiig
SexyKitten (voice)
Acting
Brian D. Johnson
OS1 Commercial Lead
Acting
Amy Adams
Amy
Acting
Matt Letscher
Charles
Acting
Spike Jonze
Alien Child (voice)
Directing
Olivia Wilde
Blind Date
Acting
David Azar
Theodore's Divorce Attorney
Acting
Guy Lewis
Marriage Counselor
Acting
Melanie Seacat
Nice Lady
Acting
Pramod Kumar
Pizza Vendor
Acting
Evelyn Edwards
Mother Who Dated Pricks
Acting
Steve Zissis
New Sweet Boyfriend of Mother Who Dated Pricks
Acting
Dane White
Son
Acting
Nicole Grother
Daughter
Acting
James Ozasky
Catherine's Dad
Acting
Samantha Sarakanti
Mother of Newborn
Acting
Luka Jones
Lewman
Acting
Gracie Prewitt
Jocelyn (Birthday Girl)
Acting
Claudia Choi
Uncomfortable Waitress
Acting
Laura Kai Chen
Tatiana
Acting
Portia Doubleday
Surrogate Date Isabella
Acting
SoKo
Isabella (voice)
Acting
Wendy Leon
Grocery Shopper
Acting
Lil Buck
Busker / Dancer
Acting
Robert Benard
Michael Wadsworth (Editor)
Acting
Lisa Cohen
Michael Wadsworth's Wife
Acting
Grant Samson
Michael Wadsworth's Associate
Art
Brian Cox
Alan Watts (voice)
Acting
Alia Janine
Commuter (uncredited)
Acting