Patrick Wilson

Will

Amy Smart

Catherine

Lynn Collins

Kate

David Ilku

Pete

Stephanie Szostak

Alex

Monique Gabriela Curnen

Janey

Frederick Weller

Kit (as Fred Weller)

Zak Orth

Josh

Rashida Jones

Nina

Janet Zarish

Pamela

Quincy Tyler Bernstine

Cali

Tim Miller

City Planning Head

Alix Elias

Waitress

Kari Swenson Riely

Lauryn

Cassidy Hinkle

Gabriella

Conor Carroll

Aaron

James Cronin

Driver

Flint Beverage

Bartender

Michael Nardella

Matt

Julia Frisoli

PTA Mom (uncredited)

Joanna Herrington

Minivan Mom (uncredited)

Jack Mulcahy

Peter Previn (uncredited)