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Kissing Jessica Stein

Play trailer Poster for Kissing Jessica Stein R 2002 1h 33m Romance Comedy LGBTQ+ Play Trailer Watchlist
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84% Tomatometer 122 Reviews 65% Popcornmeter 10,000+ Ratings
Jessica (Jennifer Westfeldt) is at the end of her emotional rope. She happens upon an intriguing personal ad, whose only drawback is that it's in the "women seeking women" section. On a daring whim, she decides to answer it. She meets funky downtown hipster Helen Cooper (Heather Juergensen) for drinks, and to her surprise, they click instantly. With conventional gender roles absent, the two women proceed to muddle through an earnest but hilarious courtship, making up the rules as they go.
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Kissing Jessica Stein

Kissing Jessica Stein

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Critics Consensus

A trite but refreshing and comical spin on nature of love.

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Critics Reviews

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Drew Gregory Autostraddle Sep 10, 2021
Jewish queer woman classic. Go to Full Review Jonathan Rosenbaum Chicago Reader Feb 3, 2009
The cast is wonderful and the story is commendably free of the sectarian us-versus-them tone of many romantic gay movies. Go to Full Review David Ansen Newsweek Aug 18, 2008
Director Charles Herman-Wurmfeld's movie knows what it wants, what its limits are, and delivers its delights accordingly. Go to Full Review Danielle Solzman Solzy at the Movies Apr 21, 2026
4/5
Twenty-five years later, Kissing Jessica Stein remains a smart, witty, and surprisingly nuanced romantic comedy. Go to Full Review Ian Thomas Malone ianthomasmalone.com Mar 27, 2025
As Helen, Juergensen brings that vital magnetic Type-A Gen X lesbian energy, the kind of force of will destined to stay with someone regardless of what happens to a relationship. Go to Full Review Samiya A. Bashir Curve May 24, 2022
Why is this film important to know about? Because we all may need the heads-up for our more Sapphically challenged friends and family who will (I promise) try to bond with us over this film. Go to Full Review Read all reviews

Audience Reviews

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bruce C @bruce999 Aug 3, 2026 dumb waste of time, stupid jokes. poor script, 'lets become a lesbian... ' i guess the movie is designed to get young folks to try experimenting, but i disliked the movie. way over-rated See more Vienna P @RT53783051 Nov 28, 2025 movie was great till 11 minutes to go, once they move in together stop watching it See more Diallo G @RT58980359 Aug 17, 2025 I love this movie! Kissing Jessica Stein is Woody Allen-esque romcom about an obsessive and overly-judgmental intellectual who can't get out of her own way, and who, in desperation, turns to a surprise connection with another woman, and has to learn how to navigate a same-sex relationship that she is in no way prepared for. It's an inspired comedy, with fully realized characters who fence with witty dialogue which, while sharp and funny on the surface, has layers beneath. The banter is delightful, funny and real, and comes embedded in situations that keeps you smiling and cringing between punchlines. The characters are so specific and believable, that even staples of the form, like the fear of ending up alone, feel compelling and deeply recognizable. I laughed, I cried, felt seen, I was comforted. Top marks! See more Stephen C @bob25009 Jul 3, 2025 Funny pride in 1 hour and 34 minutes!!!!!!!!!!!!!!!!!!!!! Rated R for Sexual Content and Language!!!!!!!!!!!!!!!!!!!!!! The USA grossed over $7,000,000.00!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! See more Jeffre L @RT26337330 Feb 9, 2024 Just one of the greatest hidden gems ever!! How could anyone not love this movie? See more BJ M @HotMovieStar Aug 17, 2023 This is a very engaging relationship movie. I enjoyed it, and it felt real. See more Read all reviews
Kissing Jessica Stein

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Cast & Crew

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Charles Herman-Wurmfeld

Director

Jennifer Westfeldt

Jessica Stein

Heather Juergensen

Helen Cooper

Scott Cohen

Josh Meyers

Tovah Feldshuh

Judy Stein

Jackie Hoffman

Joan

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Kissing Jessica Stein

Kissing Jessica Stein (2001) Kissing Jessica Stein (2001) Left to Right: Scott Cohen and Jennifer Westfeldt in KISSING JESSICA STEIN. Left to Right: Heather Juergensen and Jennifer Westfeldt in KISSING JESSICA STEIN. Left to Right: Heather Juergensen and Jennifer Westfeldt in KISSING JESSICA STEIN. Left to Right: Heather Juergensen and Jennifer Westfeldt in KISSING JESSICA STEIN. Director Charles Herman-Wurmfeld. Left to Right: Tovah Feldshuh and Jennifer Westfeldt in KISSING JESSICA STEIN. Left to Right: Heather Juergensen and Jennifer Westfeldt in KISSING JESSICA STEIN. View more photos

Movie Info

Synopsis Jessica (Jennifer Westfeldt) is at the end of her emotional rope. She happens upon an intriguing personal ad, whose only drawback is that it's in the "women seeking women" section. On a daring whim, she decides to answer it. She meets funky downtown hipster Helen Cooper (Heather Juergensen) for drinks, and to her surprise, they click instantly. With conventional gender roles absent, the two women proceed to muddle through an earnest but hilarious courtship, making up the rules as they go.
Director
Charles Herman-Wurmfeld
Producer
Eden Wurmfeld, Brad Zions, Doug Liman
Screenwriter
Heather Juergensen, Jennifer Westfeldt
Distributor
Fox
Production Co
Cineric, Michael Alden Productions
Rating
R (Sexual Content|Language)
Genre
Romance, Comedy, LGBTQ+
Original Language
English
Release Date (Theaters)
Mar 13, 2002, Wide
Release Date (Streaming)
Mar 1, 2013
Box Office (Gross USA)
$7.0M
Runtime
1h 33m
Sound Mix
Surround, Dolby Stereo, DTS
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