Self-esteem is a terrible curse on the human ego; it can force us to make incredibly poor choices, even when it takes the form of perfectionism. Jessica Stein, our heroine, suffers from that affliction and developed it early in life–her mother reminds her of the time in fifth grade when she dropped out of the lead role in a play simply because the boy playing opposite her wasn’t good enough. We see so many examples of that including one scene at a dinner party when her boss Josh (played so well by Scott Cohen) throws it right in her face by calling her after she complains that the only dates she gets are with “freaks and morons.” Couldn’t it be, he asks, that the problem is with her and not the men?
Kissing Jessica Stein (2001) is an entertaining look at single life in New York City at a time when the phrase “lipstick lesbian” was on, well, everyone’s lips. And so Ms. Stein, a cute bundle of energy played by Jennifer Westfeldt, takes a stab at the same sex, answering a personal ad from Helen (Heather Juergensen). At first repelled by her own inclination, she relaxes just enough to talk with Helen, then to kiss, then after weeks of kissing, to move on.
But while Jessica’s happier by the day with her romantic life, she still can’t bring herself to let anyone else in on the secret, always introducing Helen as her friend and making excuses for their being together. Until an unmentioned wedding brings the water to boil and the two break up. This is a romantic comedy, though it drips with political overtones, so the couple comes out of the closet and makes up–they even move in together. But there’s a reason for the term lipstick lesbian, which truly does capture the Jessica character so well, and she really wants no more than a best friend. Helen, turns out, truly is lesbian and she soon finds a better match.
In some ways this movie, which was written by Westfeldt and Juergensen, is obviously the work of inexperienced writers (it is the only produced screenplay by either), with desired plot points simply occuring more or less as needed without proper development. The direction by Charles Herman-Wurmfeld was also a bit simplistic, and also not surprising as it was his first feature film, though it did lead to better things as he was picked to direct Reese Witherspoon in the just released Legally Bonde 2. Reminds me of Damon and Affleck writing Good Will Hunting as way to get good parts for themselves.
Soctt Cohen does a really good job as the main heterosexual male. Such as the look on his face when he finds out the truth about the two women, immediately after telling Jessica how he (in so many words) loves her! I knew he looked familiar and, sure enough, a bit of peeking uncovered that he played the despicable cop Harry Denby on NYPD Blue a few years ago.
Could be that Westfeldt and Juergensen are busy doing, say, stage work but I’m quite surprised after seeing Kissing Jessica Stein that neither has done another piece of significant movie work since. Westfeldt has a role in a movie that screams “direct to cable” coming out later this year in which she shares the screen with top names like Tori Spelling and Malcolm McDowell, with not even that much shown in IMDB for Juergensen. Surprising.
Recommended
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