Theodore

Joaquin Phoenix

Amy

Amy Adams

Samantha

Scarlett Johansson

Catherine

Rooney Mara

Paul

Chris Pratt

Blind Date

Olivia Wilde

Charles

Matt Letscher

Letter Writer #1

Lynn Adrianna

Letter Writer #2

Lisa Renee Pitts

SexyKitten

Kristen Wiig

Letter Writer #3

Gabe Gomez

Alien Child

Adam Spiegel

Surrogate Date Isabella

Portia Doubleday

Text Voice

Artt Butler

Sexy Pregnant TV Star

May Lindstrom

Chat Room Friend #2 (voice)

Bill Hader

Voice of Isabella

Soko

Alan Watts

Brian Cox

OS1 Commercial Lead

Brian Johnson

Theodore's Divorce Attorney

David Azar

Mark Lewman

Luka Jones

Marriage Counselor

Guy Lewis

Dr. Johnson

Sam Jaeger

Pizza Vendor

Pramod Kumar

Nice Lady

Melanie Seacat*

Mother Who Dated Pricks

Evelyn Edwards

Busker / Dancer

Lil Buck

New Sweet Boyfriend of Mother Who Dated Pricks

Steve Zissis

Son

Dane White

Daughter

Nicole Grother

Catherine's Dad

James Ozasky

Mother of Newborn

Samantha Sarakanti

Jocelyn (Birthday Girl)

Gracie Prewitt

Uncomfortable Waitress

Claudia Choi

Tatiana

Laura Kai Chen

Grocery Shopper

Wendy Leon

Busker/Dancer

Charles "Lil Buck" Riley

Michael Wadsworth (Editor)

Robert Benard

Michael Wadsworth Wife

Lisa Cohen

Michael Wadworth's Associate

Grant Samson

Commuter

Alia Janine

OS1 Commercial Lead

Brian D. Johnson

David Salazar