Theodore

Joaquin Phoenix

Acting

Samantha (voice)

Scarlett Johansson

Acting

Letter Writer #1

Lynn Adrianna

Acting

Letter Writer #2

Lisa Renee Pitts

Acting

Letter Writer #3

Gabe Gomez

Acting

Paul

Chris Pratt

Acting

Text Voice (voice)

Artt Butler

Acting

Sexy Pregnant TV Star

May Lindstrom

Acting

Catherine

Rooney Mara

Acting

Chat Room Friend #2 (voice)

Bill Hader

Acting

SexyKitten (voice)

Kristen Wiig

Acting

OS1 Commercial Lead

Brian D. Johnson

Acting

Amy

Amy Adams

Acting

Charles

Matt Letscher

Acting

Alien Child (voice)

Spike Jonze

Directing

Blind Date

Olivia Wilde

Acting

Theodore's Divorce Attorney

David Azar

Acting

Marriage Counselor

Guy Lewis

Acting

Nice Lady

Melanie Seacat

Acting

Pizza Vendor

Pramod Kumar

Acting

Mother Who Dated Pricks

Evelyn Edwards

Acting

New Sweet Boyfriend of Mother Who Dated Pricks

Steve Zissis

Acting

Son

Dane White

Acting

Daughter

Nicole Grother

Acting

Catherine's Dad

James Ozasky

Acting

Mother of Newborn

Samantha Sarakanti

Acting

Lewman

Luka Jones

Acting

Jocelyn (Birthday Girl)

Gracie Prewitt

Acting

Uncomfortable Waitress

Claudia Choi

Acting

Tatiana

Laura Kai Chen

Acting

Surrogate Date Isabella

Portia Doubleday

Acting

Isabella (voice)

SoKo

Acting

Grocery Shopper

Wendy Leon

Acting

Busker / Dancer

Lil Buck

Acting

Michael Wadsworth (Editor)

Robert Benard

Acting

Michael Wadsworth's Wife

Lisa Cohen

Acting

Michael Wadsworth's Associate

Grant Samson

Art

Alan Watts (voice)

Brian Cox

Acting

Commuter (uncredited)

Alia Janine

Acting