

Kissing Jessica Stein
"When it comes to love, sometimes she just can't think straight."
Jessica, a Jewish copy editor living and working in New York City, is plagued by failed blind dates with men, and decides to answer a newspaper's personal advertisement. The advertisement has been placed by 'lesbian-curious' Helen Cooper, a thirtysomething art gallerist.
Trailer

Jennifer Westfeldt
Jessica Stein

Heather Juergensen
Helen Cooper

Scott Cohen
Josh Myers

Jackie Hoffman
Joan

Tovah Feldshuh
Judy Stein

Michael Mastro
Martin

Carson Elrod
Sebastian

Jon Hamm
Charles

David Aaron Baker
Dan Stein

Esther Wurmfeld
Grandma Esther

Hillel Friedman
Rabbi

Ben Feldman
Ben Feldman

Ben Weber
Larry

Brian Stepanek
Peter

Jennifer Carta
Rachel - Dan's Fiancée

Idina Menzel
Bridesmaid

Vinny Vella
Cab Driver

John Cariani
Chuck

Kevin Sussman
Calculator Guy

Jim J. Bullock
Not-Yet-Out Gay Guy
Hayden Adams
Weird Smooth Guy
Christopher Berger
Malaprops Guy

Alysia Reiner
Schuller Gallery Artist

Tibor Feldman
Roland

Michael Showalter
Stephen

Michael Ealy
Greg

Allen Fitzpatrick
Matthew

Julie Lauren
Josh's Date

Jimmy Palumbo
Cheesy Pick-up Guy #1

Ilana Levine
Helen's New Girlfriend

Naomi Scott
Seductive Woman at Gallery
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