Watch It

On DVD: Now | On Blu-ray: TBD

Kissing Jessica Stein Details


A woman searching for the perfect man instead discovers the perfect woman in this romantic comedy. Jessica Stein (Jennifer Westfeldt) is a woman with a solid career as a copy editor, but her love life isn't much to write home about; she's been through a long series of disastrous first dates that refuse to evolve into second dates, and the well-intended advice of her best friend Joan (Jackie Hoffman) and former boyfriend Josh (Scott Cohen) isn't helping a bit. One day, Jessica is scanning personal ads in the newspaper with her friends, and she sees one with a quote from her favorite poet. Jessica reads on to discover that she has a lot in common with the person who placed the ad -- too much so, since it turns out the notice is from a woman, Helen Cooper (Heather Juergensen), who manages an art gallery. Jessica figures it would at least be nice to hang out with someone who shares her interests, and she gives Helen a call. Jessica and Helen quickly strike up a close friendship that evolves into something more intimate, though neither of them has ever been involved with another woman ... and Helen is a bit more avid about her new romantic horizons than Jessica. As their relationship progresses, Jessica finds herself struggling with her feelings about her new sexual outlook, and she isn't sure how to break the news about her relationship to her mother (Tovah Feldshuh) as she tries to decide if she should bring Helen along to her brother's wedding. Kissing Jessica Stein was based on the off-Broadway play Lipschtick, which was written by Jennifer Westfeldt and Heather Juergensen, who starred in the original stage production as well as this film adaptation; the film won both the Critics' Special Jury Award and the Audience Award at the 2001 Los Angeles Film Festival. ~ Mark Deming, Rovi

  • Release date:March 13, 2002


Jennifer Westfeldt
as Jessica Stein
Heather Juergensen
as Helen Cooper
Scott Cohen
as Josh Myers
Tovah Feldshuh
as Judy Stein
Jackie Hoffman
as Joan
Michael Ealy
as Greg
Thomas Bolster
as Cheesy Pick-Up Guy
Peter Hirsch
as Stanley
Alysia Reiner
as Schuller Gallery Artist
Jennifer Carta
as Rachek, Dan's Fiancée
Michael Mastro
as Martin
Tibor Feldman
as Roland
Amy Wilson
as Bookstore Saleswoman
John Cariani
as Chuck
Naomi Sablan
as Seductive Woman At Gallery
Jimmy Palumbo
as Cheesy Pick-Up Guy
Michael Showalter
as Stephen
Vinny Vella
as Cab Driver
Christopher Berger
as Malaprops Guy
Brian Stepanek
as Peter
Hayden Adams
as Weird Smooth Guy
Jon Hamm
as Charles
Nick Corley
as Howard
Hillel Friedman
as Rabbi
Julie Lauren
as Josh's Date
Robert Ari
as Sidney Stein
Jim J. Bullock
as Not-Yet-Out Gay Guy
Carson Elrod
as Sebastian
David Aaron Baker
as Dan Stein
Esther Wurmfeld
as Grandma Esther
Idina Menzel
as Bridesmaid
Kevin Sussman
as Calculator Guy
Ilana Levine
as Helen's New Girlfriend
Adele Reichman
as Grandma Interrogating Helen
Ben Feldman
as Ben Feldman
Ben Weber
as Larry
Allen Fitzpatrick
as Matthew


Charles Herman-Wurmfeld
Brad Zions
Eden Wurmfeld
Jennifer Westfeldt
Play Author
Jennifer Westfeldt
Heather Juergensen
Play Author
Heather Juergensen
Lawrence Sher
Jim Black
Musical Direction/Supervision
Matthew Abbott
Musical Direction/Supervision
Marcelo Zarvos
Musical Direction/Supervision
Kristy Jacobs Maslin
Jason Ensler
Greg Tillman
Nate Taylor
Charlotte Bourke
Production Designer
Tema Levine
Art Director
Natalie Dierckx
Art Director
Jennifer Westfeldt
Heather Juergensen
Doug Liman
Associate Producer
Steven Firestone
Associate Producer
Eduardo Braniff
Associate Producer
Mark Pincus
Associate Producer
Stewart Griffin
First Assistant Director
Scott Keiner
First Assistant Director
James Mastracco
First Assistant Director
Susie Farris
Heidi Tannenbaum
Production Manager
Theresa Radka
Sound Mixer
George Bianchini
Steadicam Operator
Romero Lubambo
Musical Performer
Melissa Bruning
David Cerrutti
Musical Performer
Matt Janes
Line Producer
Kate Drennen
Script Supervisor
Glenn McQuaid
Title Design
Marcelo Zarvos
Musical Performer
Sheri Kornhaber
Naomi Sablan
Unit Production Manager
Gerald Donlan
Sound Editor
Connie Perelson
Location Manager
Jacob Ribicoff
Sound Editor
Dana Castro
Production Coordinator