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Jennifer Westfeldt, Heather Juergensen, Scott Cohen, Tovah Feldshuh, Jackie Hoffman ... see more see more... , Thomas Bolster , Jim J. Bullock , Tibor Feldman , Allen Fitzpatrick , Vinny Vella Sr. , Ben Weber , Julie Lauren , Michael Showalter , Kevin Sussman , Ilana Levine , Jon Hamm , John Cariani , David Aaron Baker , Idina Menzel , Michael Ealy , Robert Ari , Nick Corley , Michael Mastro , Alysia Reiner , Jennifer Carta , Brian Stepanek , Carson Elrod , Esther Wurmfeld , Hillel Friedman , Ben Feldman , Christopher Berger , Hayden Adams , Naomi Sablan , Jimmy Palumbo , Peter Hirsch , Adele Reichman , Amy Wilson , Heather Jurgensen

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... read more read more... 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

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60% liked it

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84% liked it

116 critics

R, 1 hr. 34 min.

Directed by: Charles Herman-Wurmfeld

Release Date: March 13, 2002

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DVD Release Date: September 17, 2002

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Flixster Reviews (817)

  • FrizzDrop
    November 5, 2011
    FrizzDrop
    Sexuality in film is a very delicate thing. It can either be very offputting and offends the general public and the LGBT community, or it's innovative without being condescending to the audience or just highly unrealistic. This film is full of realism, it's heartfelt and loving w... read moreith the relationship between two women, one of whom is straight to the point of repression, while the other is a free spirit who isn't defined by her sexuality in any context. Both are complete opposites in personality, history, and ethics at times. Somehow these women find a strange version of friendship and sexual upheaval, as Jessica navigates the new maze of lesbianism, and her partner becomes increasingly sexually frustrated with the antics of her Jewish princess of a girlfriend. It's a varied path for this girl who has always identified as straight, and is slowly falling into different ways to see herself. In the modern world no one has to stick to their assigned box, and so this film not only explores what it means to have sexual preference, but more importantly whether you love based on gender or based on sex. Jessica is perfectly neurotic, and her character is actually well fleshed out beyond that characteristic. She also fears failure to a great degree, which is another reason why she is so repressed and lacks the conviction to tell anyone about her new relationship. The other two principle roles are that of Jessica's ex (Cohen) and the woman she falls for (Jeurgenson). Jeurgenson and Westfeldt co-wrote the film, and act as equals throughout, always friends during the rollercoaster of their courtship. It's really remarkable while staying classically romantic and sweet. Just another example of gay going mainstream.
  • groaningbitch
    July 28, 2011
    groaningbitch
    most people would say kissng jessica stein is a lesbian version of annie hall, which is about an intelligent jewish woman's search of love and her multi-faceted viewpoints of life in new york. but to me, it's NOT. honestly, i was not interested in this picture by a look at its po... read morester, which seems like some chic-flick with cute title until one night i flipped to it on tv and watched along. then i found it is not really a chic flick. the two female leads look like real people around you, not drop-dead gorgeous like those delicious lipstick lesbians aestehticized by underground pop-culture in movies directed by david lynch or atom egoyan who seems to have an obssession with beautiful puss suddenly going gay.

    the movie's main message is simple, consider it as some thesis statement, it would be: is there any chance that a metropolitan heterosexual single woman finds love in her same sex if the men all wind up being so un-satisfactory? jessica stein, a jewish woman who works as a copy-editor in new york, is so frustrated by datings because men around her don't seem to be that thrilling or she has too many idiocyncratic principles of her own about datings. (woman could name lists of reasons why men become such a turn-off..let's skip that cliche)...un-expectedly, she answers the classified ad on the newspaper from a lesbian who wishes to recruit a date. then these two meet and find each other quite desirable and intellectually stimulating. so the lesbian tries to convince jessian stein into engaging in the lesbian lovemaking step by step. jessica lets her do it because everything about this woman is alluring except the fact she's also a woman.

    the movie tries to imbue a realistic air despite it still has one of those liberal-minded naivete from time to time. it features the parts how jessica stein has a hard time admitting to everyone and her family that the person who grants her such enormous happiness is also a woman, and the moment she holds her tears in front of her mom about this episode of her life is quite genuine. the movie emphasizes the emotional obstacle for jessica stein to confess her "temporal homosexuality" and as a matter of fact, she's also confined in her conservative mindset about gays. but eventually her family and friends accept this new change in her. (which seems quite utopic for the moment)

    the merit about this picture is its honest answer to this queer experiement of heterosexual metropolitan woman: yes, you might seek your happiness from another woman, who doesn't have all the drawbacks of the men you used to date, but life won't be happy ever after just like that. i suppose, i was wrong in the first paragraph, yes, it is a chick flick about woman looking for love, but it chooses to be honest without granting a user-frriendly, surgar-coated, falsified ending like most chick flicks. the purpose of this picture is to state the queer space is a potential utopia for heterosexual woman who is willing to cross the line for new things (let's say, banging in the other way..) just like that pop song of katy perry's, "i kiss a girl", but after you kiss a girl, then what? the girl you kiss might as well ditch you aside more violently than any depressing man who has given you a hard time.

    the movie ends with their relationship being dissolved due to the lack of sex, thus the lesbian dumps her under the reason that they behave like roommates who are nice to each other and she wants her romance with the whole "package" (which means she cannot go on without passionate sex)...so the picture finishes as two of them drinking coffee, smiling like a pair of good friends, and jessica stein is still single. at least, happily, self-sufficiently single.
  • hunterjt13
    July 14, 2011
    hunterjt13
    Disappointed with the New York dating scene, Jessica Stein embarks on a lesbian relationship, which is contrary to her upbringing and conception of herself ... no matter how right it feels.
    It's not just Jewish neuroses that hearken thoughts of Woody Allen; the structure of the l... read moreove story and ending also radiate Allen influence. Like some of Allen's films, the characters' high-energy histrionics occasionally wore on me, but the film as a whole doesn't confine itself to its influences, and the "let's take it slow" lesbian scenes are original and often subtly sexy, see especially the scene when the girls are hit on in a bar and flirt under the table. Additionally, there is one dramatic reveal in the third act that is particularly well-done.
    What the film is saying, however, is still a mystery. Is this a story about the importance of sex? the unimportance or slippery nature of societal categories? the fact that friendship must under-gird a relationship? This is not an uncomplicated romantic comedy; instead the filmmakers are trying to give us that feeling we get at the end of most of Woody Allen's films: that feeling that we saw something charming, and it was fun but also a little sad, but we're still okay with that sadness. I see Kissing Jessica Stein reaching for that feeling, but I don't think it gets there.
    Overall, Jennifer Westfeldt's bubbly neuroses and the film's sharp dialogue keep Kissing Jessica Stein a fun flick to watch, but it's not altogether light-hearted.
  • LitelBluHli
    December 22, 2010
    LitelBluHli
    I really enjoyed this movie. I've heard about it over the years, but never had the chance to watch it until it finally came in the mail via Netflix. I couldn't help, but get lost in the movie and everything about it.

    Jessica is a late 20's Jewish girl, who can't seem to find M... read morer. Right. One day she comes upon an ad for women seeking women and meets up with the other lady. It's oh so comical, yet sweet & sexy.
  • matertenebraum
    May 23, 2010
    matertenebraum
    Jessica is Jewish, uptight, slightly neurotic and single. Everyone around her is married, dating, pregnant or something and she has to take grief from her family who want to see her "happy". Try as she might she can't find a guy that she likes enough to see twice. So when she see... read mores an advertising from a woman looking for company she strangely finds herself responding and turning up to meet the bisexual Helen. The easy chat they have overcomes Jessica repulsion at the whole idea and soon they have become more than just friends. However can Jessica accept the truth herself far less be honest with others.

    This is a strange mix of a film that mostly does enough to work. In some ways it seems to be a quirky independent film but in many ways it is just an OK mainstream comedy. Jessica herself seems to be a strange mix between the neurotic side of Woody Allen, the quirky side of Ally McBeal and the female side of Bridget Jones. It is a strange mix but it more or less works as a piece of entertainment even if it isn't as sassy and fresh as it thinks it is. The relationship between Jessica and Helen is delivered in a pacey fashion that doesn't quite ring true due to the lack of depth to it but it does enough to keep things moving along. Laughs are not that common but the general amusing air carries it along and, although the romance is basic and the characters thin, they it is easy viewing and they still engage if you are in an undemanding mood.

    Westfeldt overplays her neurotic character a little bit but she just manages to keep her convincing. She has an easy chemistry with Lake which really helps cover up the lacking material they both have to deal with; it helps that they wrote it and were probably very in touch with what they were trying to do, even if they didn't necessarily do what they could have done. The rest of the cast pretty much match them in turning in workable but unspectacular performances ? not their failing but more to do with the fact that the script is breezy and light and not something a lot of depth can be brought out of. Herman-Wurmfeld's direction matches the light material and keeps it breezy.

    Overall this is a pretty sweet little film although not as fresh and fun as it thinks it is. The two leads could have done more as writers but they do have a good feel for the material and their performances help cover the material. Not many laughs or insights but it is consistently amusing and nice enough to be worth watching if you are looking for something undemanding.
  • SirPant
    September 29, 2009
    SirPant
    Not without its charm but overall less than the trailer promised!
  • jennifxu
    September 29, 2008
    jennifxu
    Cute, original, and funny. I definitely get a Woody vibe from this. But nobody does Woody like Woody, even if it is a lesbianized variation of him.
  • kiriyamakazou
    June 16, 2008
    kiriyamakazou
    A mature look at adult relationships. Failing to find the right man for her Jessica searches for a female friend. It soon blossoms into more, but the film is as simplistic as that. It questions the needs of being labeled with a sexuality and also the key components in a relations... read morehip. It's a wonderful film with well written characters that avoid stereotype, no easy accomplishment with a film filled with gays and jews. Unfortunately not being American, Lesbian or Jewish meant the film did seem rather distant and still suggests that everybody needs somebody to be complete as a man or a woman. More amusing drama than romantic comedy.
  • binky013
    January 4, 2008
    binky013
    While watching this, I kept flashing on Brokeback Mountain and thinking about how hard it is to have been in a gay relationship up until very recent times. Not that I'm guessing it's a piece of cake now for gay couples, but realizing how horrible people can be even up to ... read morethe minute I'm writing this comment, and especially in earlier portrayals, and in recent portrayals of earlier times. But as dissimilar as these two movies are in tone, there is one very striking moment of similarity.

    If you recall the journey Ledger makes back to Gyllenhaal's home, where he finds the shirts in the upstairs bedroom closet, then you may know the shared moment I'm referring to here. Gyllenhaal's mother, played by Roberta Maxwell, is the great scene stealer of the whole movie. Her knowledge of and acceptance of the relationship between Ledger and Gyllenhaal, even though she does not speak of it and shows her compassion for their plight in powerfully moving non-verbal ways, is the great moment, for me, in Brokeback. Similarly, the great moment for me in Jessica Stein is Jennifer Westfeldt's mother, played by Tovah Feldshuh, knowing of and acknowledging her daughter's love for Heather Juergensen.

    No matter how cruel people can be in any era, love, even if it is a straightforward old-fashioned mother's love, can conquer plenty -- if not necessarily all.

    Finally, I want to say that Jackie Hoffman is terrific here. I notice she isn't in the flixster actor database. I shall remedy that pronto : )
  • dreamfaeries
    November 7, 2006
    dreamfaeries
    FANTASTIC!!! LOVE IT!!!

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Critic Reviews

Jonathan Rosenbaum
February 3, 2009
Jonathan Rosenbaum, Chicago Reader

The cast is wonderful and the story is commendably free of the sectarian us-versus-them tone of many romantic gay movies. Full Review

David Ansen
August 18, 2008
David Ansen, Newsweek

Director Charles Herman-Wurmfeld's movie knows what it wants, what its limits are, and delivers its delights accordingly. Full Review

Lael Loewenstein
July 25, 2008
Lael Loewenstein, Variety

Pure pleasure. Full Review

Eric Harrison
July 21, 2005
Eric Harrison, Houston Chronicle

Westfeldt and Juergensen are both appealing actresses. Full Review

Eleanor Ringel Gillespie
November 5, 2002
Eleanor Ringel Gillespie, Atlanta Journal-Constitution

Venturesome yet unthreatening, this movie is box-office smart enough to seem cutting-edge without ever drawing blood. Full Review

Mark Caro
July 20, 2002
Mark Caro, Chicago Tribune

The good news for Jessica and the rest of us is that Kissing Jessica Stein delivers that rare combination of winning traits. Full Review

Andrew Sarris
April 11, 2002
Andrew Sarris, New York Observer

What makes the film break the relatively new gay-film formula is the wit and charm of the two actresses, who have written themselves some sparkling lines. Full Review

Jay Boyar
April 4, 2002
Jay Boyar, Orlando Sentinel

A terrific date movie, whatever your orientation.

Joe Baltake
March 29, 2002
Joe Baltake, Sacramento Bee

It wants to be thought of as a subversive little indie film, but it has all the qualities of a modern situation comedy. Full Review

Peter Rainer
March 24, 2002
Peter Rainer, New York Magazine

It all works on the level of a sprightly sitcom: lesbianism for the Lucy-and-Ethel crowd. Full Review

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    • Judy Stein: And you came home after the first day of rehearsal and said to me, 'Mommy, I'm not gonna do it. I quit.' And I said, 'Jessie, my love, why?' And you said, 'Because my co-star isn't good enough. And if my co-star isn't good enough, then the play won't be good enough. And I don't want to be part of any play that isn't good enough.' And I thought to myself, oy. This child will suffer.
    • Helen Cooper: What'd you do to be happy?
    • Jessica Stein: Nothing. I'm not.
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Kissing Jessica Stein Trivia

  • Which of the following movies is Kristin Chenoweth NOT in?  Answer »
  • what part does Idina Menzel play in Kissing Jessica Stein?  Answer »
  • In Kissing Jessica Stein, which poet does Helen quote in her personal ad?  Answer »
  • In 'Kissing Jessica Stein', where did Jessica go to college?  Answer »
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