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