Kristen Wiig

SexyKitten (voice)

Bill Hader

Chat Room Friend #2 (voice)

Artt Butler

Text Voice (voice)

Chris Pratt

Paul

Olivia Wilde

Blind Date

Scarlett Johansson

Samantha (voice)

Spike Jonze

Alien Child (voice)

Rooney Mara

Catherine

Matt Letscher

Charles

Joaquin Phoenix

Theodore

Amy Adams

Amy

Daniel Lupi

Executive Producer

Steve Zissis

New Sweet Boyfriend of Mother Who Dated Pricks

Chelsea Barnard

Executive Producer

Pramod Kumar

Pizza Vendor

Evelyn Edwards

Mother Who Dated Pricks

Lynn Adrianna

Letter Writer #1

Lisa Renee Pitts

Letter Writer #2

Gabe Gomez

Letter Writer #3

May Lindstrom

Sexy Pregnant TV Star

Brian D. Johnson

OS1 Commercial Lead

David Azar

Theodore's Divorce Attorney

Guy Lewis

Marriage Counselor

Melanie Seacat

Nice Lady

Dane White

Son

Nicole Grother

Daughter

Natalie Farrey

Executive Producer