Adam Pally as Jeff Lowry

Sarah Burns as Anne Martin

Reid Scott as Max

Catherine Reitman as Julia

Mary Grill as Beth

Kate Flannery as Principal Miller

Marceline Hugot as Joyce Lowry

Kevin Dunn as Darren Lowry

Megan Neuringer as Laura

Bobby Spears Jr. as Fellini Café Waiter

Peter Grosz as Dr. Mark Sonderskov

Christine James Walker as Hot Babe

Montana Marks as Sexy Dressed Student

Amy Londyn as Female Student

Francis Toner as Partying Teacher

Natalie Anne Pagano as Keg Standing School Nurse

Rebecca Anne Viscuse as Body Shot Girl

Chris Anthony as Good Looking Guy

Chase Hemphill as Al

Julie Mun as Carol

Sarah Van Auken as Ambivalent Girl

Gil Ozeri as Dan

Bobby Moynihan as Lenny

Cecily Strong as Amber the Ex

Schoolly D as Rapper

Angela Shelton as Michelle

Frances Callier as Robin

Devante LeYeom as Tyree

Molly Pace as Elayna

John Jensen as Johnny

Martha Stuckey as June

Pete Postiglione as Gary

Dave Ferrier as Paul

Mark Ogawa as Ricky

Daniel Reguera as Darts Opponent

Amanda Kay Livezey as Bar Waitress

David Prado as Bartender

Suzy Kaye as Carmen

Nikki Corinne Thomas as Pam

Christopher Dalbey as Wasted Guy

Amanda Damron as Diana

Michelle Mercier as Fun Girl on Bar

Sean LeeRoy as Good Looking Meathead

Chase Bowman as Guy at Door #1

David Beaver as Guy at Door #2

Matthew Andrews as Guy at Door #3

Maeve W. Joyce-Argott as Maeve

Hollie Schwarz as Brunch Waitress

Greg Wood as Prisoner of Love Narrator (voice)

Thomas Leonard as Bar Drunk

Rachel Johnston as Model Date

Patti Davidson-Gorbea as Phone Message Stacy

Carlos Delgado as Furniture Repo Guy #1

Lou Rosmini as Furniture Repo Guy #2

Dana Kreitz as Lara

Charlie McDermott as Student in Guidance Office

Gary Ayash as Teacher in Car

Aaron Benjamin Miller as Random Guy

George Williams as Party Guy 1 (uncredited)