Kissing Jessica Stein

Jennifer Westf...

as

Jessica Stein

Heather Juerge...

as

Helen Cooper

Scott Cohen

as

Josh Myers

Jackie Hoffman

as

Joan

Tovah Feldshuh

as

Judy Stein

Michael Mastro

as

Martin

Carson Elrod

as

Sebastian

Jon Hamm

as

Charles

David Aaron Ba...

as

Dan Stein

Esther Wurmfeld

as

Grandma Esther

Hillel Friedman

as

Rabbi

Ben Feldman

as

Ben Feldman

Ben Weber

as

Larry

Brian Stepanek

as

Peter

Jennifer Carta

as

Rachel - Dan's...

Idina Menzel

as

Bridesmaid

Vinny Vella

as

Cab Driver

John Cariani

as

Chuck

Kevin Sussman

as

Calculator Guy

Jim J. Bullock

as

Not-Yet-Out Ga...

Hayden Adams

as

Weird Smooth G...

Christopher Be...

as

Malaprops Guy

Alysia Reiner

as

Schuller Galle...

Tibor Feldman

as

Roland

Michael Showal...

as

Stephen

Michael Ealy

as

Greg

Allen Fitzpatr...

as

Matthew

Julie Lauren

as

Josh's Date

Jimmy Palumbo

as

Cheesy Pick-up...

Ilana Levine

as

Helen's New Gi...

Naomi Scott

as

Seductive Woma...