Red Oaks

Craig Roberts

David

Alexandra Socha

Skye

Paul Reiser

Getty

Oliver Cooper

Wheeler

Gage Golightly

Karen

Ennis Esmer

Nash

Jennifer Grey

Judy

Richard Kind

Sam Meyers

Josh Meyers

Barry

Alexandra Turshen

Misty

Freddie Roman

Herb

Gina Gershon

Fay Getty

Nate Smith

Skip

Lev Pakman

Six Pack

Nick Bailey

Steve Lefevre

Willem Marx

Rizzo

Jessica Hecht

Rebecca Horowitz

Annabelle Dexter-Jones

Xan

Ann Carr

Gail

James Waterston

Dr. Dale Blum

Rachel Feinstein

Jean Blum

David Fierro

Ganz

Mark Linn-Baker

Rabbi Ken

Juliet Brett

Tabitha

John Hodgman

Travis

Deborah Fennelly

Yvonne

Reggie Alvin Green

Reggie / Shoe Shiner

Beth Stelling

Margot

Greer Barnes

Terry

Shane Nepveu

Eli

Christopher Innvar

Lawyer

Richard Masur

Morrie

Anne O'Sullivan

Hinda

Rick Crom

Club Member / Older Man

Adriana DeGirolami

Kimberly

Murielle Telio

Dawn

Brandon Kyle Goodman

Alex

Jared Loftin

Zach Levine

Jacob Storms

Serge

Will Roland

Joel

Tom Papa

Dental Instructor

Kathy Searle

Agatha

Patrick Garner

Judge

John Reynolds

Bartender

Brady Dowad

Etienne

Mackenzie Lansing

Claire

Rita Duran

Cabaret Club Patron (uncredited)

Cliff Moylan

Federal Agent #1

Marc Damon Johnson

Federal Agent #2

Jeremy Shinder

Jeffrey Glassman

Elise Rovinsky

Witness

Roe Hartrampf

Mark

Rudy De La Cruz

Taco

Brett Tabisel

Waiter

Richard DeDomenico

Elderly Guest #1

Maria Aparo

Female Sex Show Performer

Duke Valenti

Beat Cop

Brian Silliman

Night Security Guard

Amanda Azarian

Dominatrix (uncredited)

Glenn Kubota

Old Japanese Chef

Ai Kiyono

General Manager

Joe Lanza

Classmate #1

Doris McCarthy

Luncheon Guest (uncredited)

J.D. Lawrence

Cook

Nat Cassidy

Sous Chef

Sean Crespo

Golfer

Amelia Workman

Party Guest

Sudi Green

Pam

Christian Capozzoli

Wall Streeter

Akaash Singh

Delivery Guy

Barry Godin

Dr. Alan Kornblatt

Patricia Buckley

Mrs. Kornblatt

Carolyn Baeumler

Deborah Gorman

Jacob Berger

Marvin Gorman

Barry Papick

Foreman

Kelly Aaron

Wedding Guest (uncredited)

Tate Donovan

Martin van Diem

Chris Monty

Golfing Member

Max Sheldon

Brett van Diem

Alan Aisenberg

Alan

Yuval Boim

Doctor

Brian Sullivan

Pool Patron

Lana Yoo

Korean Nurse

Hyten Davidson

Flirty Bikini Girl (uncredited)

Frank Deal

Skip (uncredited)

John Quilty

Member 1 (uncredited)

Wally Dunn

Divorce Lawyer

Annie Henk

Admissions Officer

John O'Creagh

Administrator

Alix Cross

Jennifer Horowitz (uncredited)

Grayson Eddey

Young David (uncredited)

Miriam A. Hyman

Janice

Mollie Heckerling

Bar Patron

Caleb Wells

Ricky

Daniel Garcia

Father (uncredited)

Brandy Gardener

Fern Bar Patron (uncredited)

Brittini Schreiber

Friend (uncredited)

Michael Cumpsty

Priest

James Cusati-Moyer

Simon

Emmit George

Bailiff

Dave T. Koenig

Mr. Cohen

Suzanne Savoy

Adelaide

Selena Coppock

Rhonda

Nina Grollman

Suburban Mom

Raymond J. Lee

Peter

Andrea Frierson

Female Clerk

Laura Knight

ER Nurse

Matthew F. O'Connor

Pawn Broker

Twinkle Burke

Nurse

Caleb Wells

Ricky

Buzz Roddy

Jury Foreman