Characters played by Jennifer Westfeldt
Jessica Stein
Characters played by Tovah Feldshuh
Judy Stein
Characters played by Heather Juergensen
Helen Cooper
Characters played by Esther Wurmfeld
Grandma Esther
Characters played by Hillel Friedman
Rabbi
Characters played by Ben Feldman
Self
Characters played by Robert Ari
Sidney Stein
Characters played by David Aaron Baker
Dan Stein
Characters played by Jennifer Carta
Rachel - Dan's Fiancée
Characters played by Ben Weber
Larry
Characters played by Brian Stepanek
Peter
Characters played by Nick Corley
Howard
Characters played by Jackie Hoffman
Joan
Characters played by John Cariani
Chuck
Characters played by Scott Cohen
Josh Meyers
Characters played by Christopher Berger
Malaprops Guy
Characters played by Hayden Adams
Weird Smooth Guy
Characters played by Kevin Sussman
Calculator Guy
Characters played by Jim J. Bullock
Not-Yet-Out Gay Guy
Characters played by Alysia Reiner
Schuller Gallery Artist
Characters played by Carson Elrod
Sebastian
Characters played by Michael Mastro
Martin
Characters played by Tibor Feldman
Roland
Characters played by Michael Showalter
Stephen
Characters played by Michael Ealy
Greg
Characters played by Naomi Scott
Seductive Woman at Gallery
Characters played by Jon Hamm
Charles
Characters played by Allen Fitzpatrick
Matthew
Characters played by Julie Lauren
Josh's Date
Characters played by Jimmy Palumbo
Cheesy Pick-up Guy #1
Characters played by Thomas L. Bolster
Cheesy Pick-up Guy #2
Characters played by Vinny Vella
Cab Driver
Characters played by Peter Hirsch
Stanley
Characters played by Idina Menzel
Bridesmaid
Characters played by Adele Reichman
Grandma Interrogating Helen
Characters played by Amy Wilson
Bookstore Saleswoman
Characters played by Ilana Levine
Helen's New Girlfriend
Characters played by Dalit Berkowitz
Barfly
Characters played by Lee Kheel
Old Woman at Antique Store
Characters played by Marshall Dancing Elk Lucas
Guy