Kissing Jessica Stein (2001)
- Starring:
- Jennifer Westfeldt, Heather Juergensen, (more)
- Director(s):
- Charles Herman-Wurmfeld
- Theatrical MPAA Rating:
- R
- Category:
- Romance
My RatingTheatrical Release Information | See Details About All Versions
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, All Movie Guide
- Theatrical Feature Running Time:
- 97 mins
Complete Cast:
- Jennifer Westfeldt - Jessica Stein
- Scott Cohen - Josh Myers
- Jackie Hoffman - Joan
- Jim J. Bullock - Not-Yet-Out Gay Guy
- Allen Fitzpatrick - Matthew
- Ben Weber - Larry
- Michael Showalter - Stephen
- Ilana Levine - Helen's New Girlfriend
- John Cariani - Chuck
- Idina Menzel - Bridesmaid
- Robert Ari - Sidney Stein
- Michael Mastro - Martin
- Brian Stepanek - Peter
- Esther Wurmfeld - Grandma Esther
- Ben Feldman - Ben Feldman
- Hayden Adams - Weird Smooth Guy
- Jimmy Palumbo - Cheesy Pick-Up Guy
- Adele Reichman - Grandma Interrogating Helen
- Jennifer Carta - Rachek, Dan's Fiancée
- Heather Juergensen - Helen Cooper
- Tovah Feldshuh - Judy Stein
- Thomas Bolster - Cheesy Pick-Up Guy
- Tibor Feldman - Roland
- Vinny Vella - Cab Driver
- Julie Lauren - Josh's Date
- Kevin Sussman - Calculator Guy
- Jon Hamm - Charles
- David Aaron Baker - Dan Stein
- Michael Ealy - Greg
- Nick Corley - Howard
- Alysia Reiner - Schuller Gallery Artist
- Carson Elrod - Sebastian
- Hillel Friedman - Rabbi
- Christopher Berger - Malaprops Guy
- Naomi Sablan - Seductive Woman At Gallery
- Peter Hirsch - Stanley
- Amy Wilson - Bookstore Saleswoman
- Director(s):
- Charles Herman-Wurmfeld
- Writer(s):
- Jennifer Westfeldt, Heather Juergensen
- Producer(s):
- Brad Zions, Eden Wurmfeld
- Theatrical MPAA Rating:
- R(Adult Language, Sexual Situations, Not For Children, Adult Situations)
- Categories:
- Romance
- Closed Captioning:
- Check All Versions
- Subtitles:
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