Adam Pally

Jeff Lowry

Sarah Burns

Anne Martin

Reid Scott

Max

Catherine Reitman

Julia

Mary Grill

Beth

Kate Flannery

Principal Miller

Marceline Hugot

Joyce Lowry

Kevin Dunn

Darren Lowry

Megan Neuringer

Laura

Bobby Spears Jr.

Fellini Café Waiter

Peter Grosz

Dr. Mark Sonderskov

Christine James Walker

Hot Babe

Montana Marks

Sexy Dressed Student

Amy Londyn

Female Student

Francis Toner

Partying Teacher

Natalie Anne Pagano

Keg Standing School Nurse

Rebecca Anne Viscuse

Body Shot Girl

Chris Anthony

Good Looking Guy

Chase Hemphill

Al

Julie Mun

Carol

Sarah Van Auken

Ambivalent Girl

Gil Ozeri

Dan

Bobby Moynihan

Lenny

Cecily Strong

Amber the Ex

Schoolly D

Rapper

Angela Shelton

Michelle

Frances Callier

Robin

Devante LeYeom

Tyree

Molly Pace

Elayna

John Jensen

Johnny

Martha Stuckey

June

Pete Postiglione

Gary

Dave Ferrier

Paul

Mark Ogawa

Ricky

Daniel Reguera

Darts Opponent

Amanda Kay Livezey

Bar Waitress

David Prado

Bartender

Suzy Kaye

Carmen

Nikki Corinne Thomas

Pam

Christopher Dalbey

Wasted Guy

Amanda Damron

Diana

Michelle Mercier

Fun Girl on Bar

Sean LeeRoy

Good Looking Meathead

Chase Bowman

Guy at Door #1

David Beaver

Guy at Door #2

Matthew Andrews

Guy at Door #3

Maeve W. Joyce-Argott

Maeve

Hollie Schwarz

Brunch Waitress

Greg Wood

Prisoner of Love Narrator (voice)

Thomas Leonard

Bar Drunk

Rachel Johnston

Model Date

Patti Davidson-Gorbea

Phone Message Stacy

Carlos Delgado

Furniture Repo Guy #1

Lou Rosmini

Furniture Repo Guy #2

Dana Kreitz

Lara

Charlie McDermott

Student in Guidance Office

Gary Ayash

Teacher in Car

Aaron Benjamin Miller

Random Guy

George Williams

Party Guy 1 (uncredited)