Theodore

Samantha (voice)

Letter Writer #1

Letter Writer #2

Letter Writer #3

Paul

Text Voice (voice)

Sexy Pregnant TV Star

Catherine

Chat Room Friend #2 (voice)

SexyKitten (voice)

OS1 Commercial Lead

Amy

Charles

Alien Child (voice)

Blind Date

Theodore's Divorce Attorney

Marriage Counselor

Nice Lady

Pizza Vendor

Mother Who Dated Pricks

New Sweet Boyfriend of Mother Who Dated Pricks

Son

Daughter

Catherine's Dad

Mother of Newborn

Lewman

Jocelyn (Birthday Girl)

Uncomfortable Waitress

Tatiana

Surrogate Date Isabella

Isabella (voice)

Grocery Shopper

Busker / Dancer

Michael Wadsworth (Editor)

Michael Wadsworth's Wife

Michael Wadsworth's Associate

Alan Watts (voice)

Commuter (uncredited)