Patrick Wilson

Will

Amy Smart

Catherine

Lynn Collins

Kate

David Ilku

Pete

Susie Stewart Rubio

Meg (as Susan Stewart)

Stephanie Szostak

Alex

Mark Setlock

Sam

Monique Gabriela Curnen

Janey

Frederick Weller

Kit (as Fred Weller)

Zak Orth

Josh

Rashida Jones

Nina

Janet Zarish

Pamela

Troy Britton Johnson

Stewart

Kevin Rosseljong

Nate

Quincy Tyler Bernstine

Cali

Jennifer Smolos

Cynthia

Tim Miller

City Planning Head

Alix Elias

Waitress

Kelly Nyks

Aiden

Kari Swenson Riely

Lauryn

Cassidy Hinkle

Gabriella

Conor Carroll

Aaron

Teresa Woods

Jenny

Darren Johnson

Man in Suit 1

Stephen Niese

Man in Suit 2

Kevin C. Loomis

Man in Suit 3

James Cronin

Driver

Flint Beverage

Bartender

David Lavine

Simon

Shira Flam

Woman

Michael Nardella

Matt

Scott Abbondanzo

Boy Playing Soccer (uncredited)

Memory Contento

Betsey (uncredited)

Paul Eichel

Tom (uncredited)

Kyle Fischbach

Boy in Minivan (uncredited)

Julia Frisoli

PTA Mom (uncredited)

Joanna Herrington

Minivan Mom (uncredited)

Ben Hersey

Ben (uncredited)

Halen D. Isbell

Connor (uncredited)

Raziel Jordan

Michael (uncredited)

Matthew Martini

Guy driving red convertible (uncredited)

Jack Mulcahy

Peter Previn (uncredited)