Review: Kissing Jessica Stein (2001)

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(warning: review contains spoilers)

With Jennifer Westfeldt’s new movie ‘Friends with Kids’ opening last weekend, I thought it would be a good time to look back at her breakthrough 2001 independent film ‘Kissing Jessica Stein’ which she co-wrote (from her own co-written play) and starred in.

Westfeldt plays the title character, an uptight, repressed hetrosexual woman in her late 20s, who has abandoned her artistic talent for the safety of an office job. She’s also had little romantic success, mainly because her standards are always impossibly high. All that changes when – despite having no history of lesbianism – she responds to a personal ad from a woman, Helen (Heather Juergensen, who co-wrote the script with Westfeldt). Helen  is everything Jessica isn’t  – confident, comfortable in her sexuality (she’s bisexual) with a career she’s passionate about.

Despite their opposite characteristics (or perhaps because of), they hit it off and their relationship has inevitably major ramifications for not only them, but friends and family.

On the surface, KJS doesn’t feel particularly promising as its indy status hides some rather corny and contrived elements. An early montage of failed dates Jessica goes through is dispiritingly sitcomish as the men are all the depicted as one-note dolts. This is misguided, lazy writing not only because it isn’t witty but it doesn’t allow a demonstration of what we’re constantly told in the film is one of Jessica’s key persona traits – that she’s too fussy and uptight when it comes to finding the right partner.

While the feeling of contrivance never quite leaves the film, KJS is overall a charming and likable film. When it settles down to treating the array of central characters and various plights seriously, it does so with depth and humour.

Most significant is how the film treats the relationship between Jessica and Helen – if the concept that these two could become romantically involved isn’t convincing than the film would sink. But there’s such charisma and chemistry between the two that it never becomes an issue.

There are also strong supporting characters. Particularly notable is Jessica’s boss and ex-boyfriend Josh (excellently played by Scott Cohen), probably the most interesting character in the film. He regularly delivers acidic comments towards Jessica (although usually quite astute) but the more we see of him the more we realise this contempt is driven by a despair that his relationship with Jessica ended and the faint hope that he can reunite with her. Thanks to Cohen’s fine performance, this character rings particularly true.

Then there is Jessica’s mother Judy (Tovah Feldshuh). Initially she seems a stereotypical overbearing Jewish mother but the further the film progresses the more substance and interest she provides. This helps make a scene late in the movie where Judy has a heart-to-heart with her daughther genuinely emotionally moving and the high point of the film.

KJS has attracted criticism for its finale where – after overcoming enormous obstacles to become a couple – Jessica and Helen break-up and become just good friends. While many saw this as a copout I thought it was actually quite truthful because despite their chemistry, there were significant issues between the two (especially in terms of sexuality and desire) that made it rather unlikely they would prosper long-term. Quite cunningly, despite the breakup the film ends on a fairly upbeat note so that it’s both honest and crowd-pleasing.

While there is much good work on display in KJS, one shouldn’t overpraise it (as often can occur when a small film like this gains surprising popularity) as it always has an element of superficiality to it. To use one example, when we see Jessica expressing bemused negativity towards yoga, meditation and chanting early on in the film, one just knows that by the end we’ll see an obligatory scene where she meditates to demonstrate her liberated self. And that her liberating romance with Helen triggers her going back to her true talent of painting is rather simplistically portrayed.

KJS is by no standards groundbreaking cinema and  despite its independent status, is basically a conventional, light romantic comedy with a twist. But in a genre full of bland and dreary efforts, KJS stands out as pleasing, amusing and entertaining and one should be thankful for that.

Rating: B

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