Jennifer Westfeldt as Jessica Stein

Heather Juergensen 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 Baker 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 Fiancée

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 Gay Guy

Hayden Adams as Weird Smooth Guy

Christopher Berger as Malaprops Guy

Alysia Reiner as Schuller Gallery Artist

Tibor Feldman as Roland

Michael Showalter as Stephen

Michael Ealy as Greg

Allen Fitzpatrick as Matthew

Julie Lauren as Josh's Date

Jimmy Palumbo as Cheesy Pick-up Guy #1

Ilana Levine as Helen's New Girlfriend

Naomi Scott as Seductive Woman at Gallery