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Kissing Jessica Stein
Directed by: Charles Herman-Wurnfeld
Written by: Heather Juergensen, Jennifer Westfeldt
Starring: Jennifer Westfeldt, Heather Juergensen, Scott Cohen, Tovah Feldshuh
Language: English
Look for it at the video store under: comedy
Watch it when you’re in the mood for something: lovey, quintessentially quasi-adult, witty
The critic says: / 5 the rating system explained
Fun factor: /5

Plot synopsis Smart, attractive Jessica Stein (Westfeldt) is the quintessential neurotic single woman living in New York. She has a solid job and a gorgeous apartment, as well as great friends and a loving family — none of whom can understand why someone as terrific as Jessica can’t seem to find a nice guy and settle down. But Jessica is just plain tired of the dating scene. In a short montage, it becomes evident that she’s searched every nook and cranny of the city for a suitable man, and her patience for jerks, tightwads, and outright nutjobs is running low. A colleague shows her a personal ad, the author of which sounds like a perfect match for Jessica. Unfortunately, the oh-so-perfect ad has just one hitch: it’s aimed at women-seeking-women, something Jessica is not. But in an act of courage, she uncharacteristically throws caution to the wind and agrees to meet this possible soulmate. The writer of the ad turns out to be Helen Cooper (Juergensen), a hip, sexually-open woman who is also testing the lesbian waters. Upon their first meeting, it’s clear that they’re a match made in midtown—Helen’s flip and carefree attitude complements Jessica’s relationship hang-ups better than any man ever has. After an awkward first kiss, Jessica’s hooked. She and Helen embark on a relationship that is spontaneous and new, yet carefully contrived. Jessica’s hesitancy to allow Helen to participate in certain aspects of her life leads the pair to question if their relationship can survive in a dominantly hetero world, and whether Jessica can cope with romance sans a man.

Review Kissing Jessica Stein made me want to be a lesbian, pure and simple. I mean, what’s better than hanging with your best friend, lounging in bed all day, then meandering down to the corner market to buy brunch fixins’? However, while Kissing Jessica Stein explores the wonderful eccentricities of girl-girl love, it also allows that lesbianism might not be for everyone. Jessica has major issues with her new status as girlfriend-to-a-girlfriend, and her neuroses about relationships and expectations are hilariously honest. The make-out scenes between Jessica and Helen are cringe-worthy and riotous, evoking the kind of faux intimacy and awkwardness of sixth-grade Spin the Bottle. This modern take on sex and the single woman is fresh and stylish, albeit a tad predictable. While there is some believability to Jessica’s concerns about coming out, the reactions of her friends and family are far-fetched – they’re unanimously, instantly understanding and accepting of the news that Jessica and Helen aren’t just friends but lovers, in a way that’s all very happy and nice, but just doesn’t ring true. Furthermore, Jessica’s inability to choose between Helen and ex-boyfriend/boss Josh (Cohen) seems to demonstrate the pristine coolness of switching teams. To a straight person this is perhaps understandable and fun, but I wonder how the gay world feels about this kind of wavering. Still, while Kissing Jessica Stein follows the schema of the archetypical romantic comedy, it makes up for its weaknesses with wit and indisputable flavor.—reviewed by Bridget Huffine

Bridget Huffine (bridgeth@hotmail.com) is a freelance writer living in Denver, with dreams of relocating to the Big Apple in the near future. She spends the cold Colorado winters curled up on the couch, watching videos, maniacally applying rhinestones to anything and everything.

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