Kissing Jessica Stein


Kissing Jessica Stein

Critics Consensus

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



Total Count: 120


Audience Score

User Ratings: 16,544
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Movie Info

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


Jennifer Westfeldt
as Jessica Stein
Heather Juergensen
as Helen Cooper
Tovah Feldshuh
as Judy Stein
Scott Cohen
as Josh Myers
Esther Wurmfeld
as Grandma Esther
Carson Elrod
as Sebastian
Ben Feldman
as Himself
Robert Ari
as Sidney Stein
Jennifer Carta
as Rachel, Dan's Fiancee
Ben Weber
as Larry
Christopher Berger
as Malaprops Guy
Hayden Adams
as Weird Smooth Guy
Kevin Sussman
as Calculator Guy
Jim J. Bullock
as Not-Yet-Out Gay Guy
Alysia Reiner
as Schuller Gallery Artist
Naomi Sablan
as Seductive Woman At Gallery
Jon Hamm
as Charles
Julie Lauren
as Josh's Date
Jimmy Palumbo
as Cheesy Pick-up Guy No.1
Thomas Bolster
as Cheesy Pick-up Guy No. 2
Vinnie Vella
as Cab Driver
Vinny Vella Sr.
as Cab Driver
Peter Hirsch
as Stanley
Idina Menzel
as Bridesmaid
Adele Reichman
as Grandma Interrogating Helen
Amy Wilson
as Bookstore Saleswoman
Ilana Levine
as Helen's New Girlfriend
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Critic Reviews for Kissing Jessica Stein

All Critics (120) | Top Critics (34) | Fresh (100) | Rotten (20)

Audience Reviews for Kissing Jessica Stein

  • Jul 15, 2012
    I have a girl crush on Jennifer Westfeldt (which seems appropriate for this movie about a buttoned-up Jewess trying on lesbianism to find her [7] true love[s]). Too bad she's all in a committed long-term relationship with hunk-o-man Jon Hamm. Westfeldt as Jessica is so adorably neurotic and girl-next-door-pretty. My perennial favorite, Scott Cohen, is mean and tough but also sweetly anguished. Jessica and Helen's romance blossoms awkwardly and hilariously at first, but the moment Jessica comes over to take care of Helen when she's sick is a nice turning point. The movie debates homosexual politics a bit, but it doesn't end with a clear message about whether one should be with her own sex or the other. It also doesn't cheapen Jessica's lesbian relationship as a dalliance. I also love how the script sneaks in bunches of word-nerd humor and suffering artist philosophy. Judy's monologue about how Jessica quitting the school play because she thought her costar wasn't good enough - and only really hurting herself - is a metaphor for her dating life is eloquent and insightful. Josh's realization at his happiness for Jessica's painting and his own novel writing is a necessary reminder for all creative artists. Blech.
    Alice S Super Reviewer
  • Jul 09, 2012
    An interesting look at this kind of situation.
    Sarah P Super Reviewer
  • Feb 21, 2012
    Just a really inspirational movie. It's all worth it for the single scene where Helen is sick.
    Letitia L Super Reviewer
  • Nov 05, 2011
    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 with 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.
    Spencer S Super Reviewer

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