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Jessica Stein (Jennifer Westfeldt) aspires to be a painter, but works as a copy editor at a New York magazine. Her boss, Josh (Scott Cohen), whom she once dated, is particularly harsh toward the talkative and fidgety Jessica. Disillusioned with her dates, she responds to a notice in the personals column placed by the coolly confident Soho gallery assistant Helen (Heather Juergensen). They strike up a friendship which leads to trysts on the couch, the bed and eventually moving in together. As the nature of Jessica and Helen’s relationship dawns on Jessica’s close-knit Jewish family and the increasingly prickly Josh, the pair realise what ties them together.

Review by Louise Keller:
Smart and sassy, Kissing Jessica Stein is a warm and playful romantic comedy where sexuality plays as large a role as any leading character. This is not a traditional romance where girl meets boy, or indeed where girl meets girl, but an exploration of relationships. The actual gender of the character concerned is a secondary consideration, making this adventure of the heart a sweet and delectable journey for anyone of any sexual persuasion. Jennifer Westfeldt and Heather Juergensen have teamed up to pen, produce and star in this enchanting and surprising outing (pun intended). The script is finely honed with just the right mix of humour and substance, and Westfeldt in particular sparkles in the title role. Looking like a prettier Lisa Kudrow, her comic delivery is equally appealing, as she makes us believe and understand her perfection-seeking Jessica. Just like My Big Fat Greek Wedding’s Toula, whose all-embracing family wants her married to ‘a nice Greek boy,’ Jessica’s family is eager that she marries ‘a nice Jewish’ one. The other parallel between them is that both are independent film successes, with a non-star cast. But that’s where the similarity ends, and Kissing Jessica Stein manages to slip comfortably from flippant satire to weighty issues of commitment smoothly. The handling of serious issues is intelligently intertwined with the humour, and the snap-edited scenes where we meet Jessica’s dates are beautifully executed. Jammed together they may appear far-fetched, but in actual fact, they are based on real people, real dates. In total contrast, the heart-to-heart between Jessica and her mother (Tovah Feldshuh, stunning), jolts all our emotions, delivering the film’s most moving moment. Much like Helen’s multi-layered lipstick, the girls take a multi-layered approach to the relationship, with friendship as the base, companionship at the centre and sex as the topping. A special mention on the casting and performance of the magnificent Jackie Hoffman, whose quirky, pregnant best friend is simply an unexpected pleasure filled with surprises. With its wonderful jazz soundtrack of Blossom Dearie, Sarah Vaughan, Ella Fitzgerald, Dinah Washington, Peggy Lee and Billie Holiday standards, and crisp New York settings, it’s easy to be seduced. A genuinely sweet and uplifting film with plenty of spirit, Kissing Jessica Stein is a delight.

Review by Richard Kuipers:
A mildly entertaining romantic comedy, Kissing Jessica Stein has a good heart but not enough laughs or substance to make the distance. The idea - developed from a stage skit by writers and co-stars Heather Juergensen and Jennifer Westfeldt - is a good one. Exploring gender issues from the perspectives of two essentially straight but bi-curious females lends this fresh and engaging appeal at the outset. A bright opening finds 28 year-old Jessica harassed by her very Jewish family for not being married - 'shut up, I'm atoning' is the sharp reply as her mother and grandmother attempt to match-make at a synagogue service. There's a lively step to this as our heroine goes through a quick-edit sequence of disastrous dates you'll find in just about every indie film on the topic before finally plucking up the courage to answer Helen's newspaper ad. Unfortunately the film loses a lot of steam once Jessica and arty-type Helen get down to the nitty gritty of discussing (and doing) the physical side of their relationship. Scenes that are way overlong and don't say much slow the pace down and there are several points at which Jessica is so confused and evasive that Helen's continued interest doesn't make much dramatic sense. The filmmakers don't have a pro or con line to push regarding lesbian lifestyle and they achieve their goal of making us less concerned with the like gender of the protagonists than with their observations of universal romantic foibles. I would like to have cared more about the fate of Jessica and Helen but I found their actions and motivations harder to accept the longer it played. The courtship here is good, the consummation less so.

Review by Paul Kalina:
Annie Hall redux might have been the subtitle of this barely watchable romantic comedy - troublingly, it’s making a concerted bid for the crown as 2002’s sleeper hit — about the complications that follow when the relationship between a straight, neurotic, Jewish 20-something and a sexually aware, straight woman spills over from platonic friendship into sexual intimacy. Kissing Jessica Stein thrusts us into an instantly recognisable milieu. It glimpses the landmarks and sidewalks of Manhattan familiar from hundreds of films and TV shows (sadly, however, without any of the visual splendour that Gordon Willis gave it in Woody Allen’s films), the doting, overbearing Jewish mother (the broad but amusing Tovah Feldshuh) who frets because her daughter hasn’t yet wed a doctor, the comical confrontations of the dating scene and Will and Grace-style gender-bender mix-ups. It’s all mixed through with smart, sassy and self-deprecating New York Jewish humour. At its heart, Kissing Jessica Stein confronts one of the perennial riddles of movies and television shows in the 1990s; is friendship or sex the bond that drives enduring and loving relationships? What’s odd about this girl-meets-girl story is that Jennifer Westfeldt and Heather Juergensen, who wrote the script and play, respectively, Jessica and Helen, skim right past the sexual dynamics of the situation they have stumbled into. “Today sexual preference, tomorrow henna tattoos”, one character wryly quips, a remark that perfectly sums up the casual nonchalance with which, they’d have us believe, 20-somethings flirt with sexual identity. But by refusing to fathom the topics that nibble at the edge of this film, the resolution, which we can see from a thousand yards, comes across as a highly pat contrivance. Admittedly, there is some wonderful banter in this film, much of it filled with ripe sexual innuendo, such as when Helen’s gay friends discuss the relative merits of their friend’s flirtation with homosexuality. But much of this film, far too much indeed, is content to simply recycle romantic set-ups, restate its own smartness or repeat some self-satisfied quirk, particularly in the case of Westfeldt’s increasingly forced and grating mannerisms. There’s nothing here that hasn’t been tried in any one of scores of 1990s sitcoms, and anyone who has fretted over the ‘sitcom-isation’ of recent cinema may fast discover their worst fears coming true as they watch this.

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CAST: Jennifer Westfeldt, Heather Juergensen, Scott Cohen, Tovah Feldshuh, Jackie Hoffman

PRODUCER: Eden Wurmfeld, Brad Zions

DIRECTOR: Charles Herman-Wurmfeld

SCRIPT: Heather Juergensen, Jennifer Westfeldt


EDITOR: Kristy Jacobs Maslin, Greg Tillman

MUSIC: Marcelo Zarvos


RUNNING TIME: 97 minutes


AUSTRALIAN RELEASE: November 7, 2002

VIDEO DISTRIBUTOR: Fox Home Entertainment

VIDEO RELEASE: March 19, 2003 (also on DVD)

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