Kissing Jessica Stein

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Kissing Jessica Stein

R,

2002,

1h 33m,

Romance/

Comedy/

LGBTQ+

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84%

122 Reviews

Tomatometer

65%

10,000+ Ratings

Popcornmeter

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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Critics Consensus

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

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Drew Gregory

Autostraddle

Sep 10, 2021

Jewish queer woman classic.

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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.

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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.

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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.

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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.

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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.

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Kylo R

Apr 29, 2018

It's that kind of movie that at the end I have to ask myself: did I see it before? So the cases are two. One: I did and I cannot even remember it (so it is very forgettable). Two: I did not, but it felt like I did (so does not bring anything new to me). So it does not matter, because at the end I have to give a low mark to it (and try to avoid it's vision for the 3rd time)

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Hagrid S

Dec 25, 2017

I appreciate the story going beyond the honeymoon phase of the relationship. We get to see the main character grow even more.

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Hagrid R

Jan 6, 2017

Cute show but the script needed a little work and the directing was weak. I could have really enjoyed this movie if the scenes weren't so harried.

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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

Orchestra Seats

74%

70%

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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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