Kissing Jessica Stein

Kissing Jessica Stein

97 mins | Comedy | March 13, 2002

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.

Kissing Jessica Stein

97 mins | Comedy | March 13, 2002

Kissing Jessica Stein
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.
IMDb rating 6.5
Producers Fox Searchlight Pictures, Eden Wurmfeld Films, Cineric, Michael Alden Productions, Brad Zions Films
Original title Kissing Jessica Stein
Directors Kate Drennen, Charles Herman-Wurmfeld
Writers Jennifer Westfeldt, Heather Juergensen

Cast

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 Self

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