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Kissing Jessica Stein

Starring Heather Juergensen and Jennifer Westfeldt
Screenplay by Heather Juergensen and Jennifer Westfeldt
Directed by Charles Herman-Wurmfeld
Official website

IN SHORT: "Even between the closest human beings infinite distances continue to exist." So sleep with a friend. [Rated R for sexual content and language. 96 minutes]

How do you make a movie that includes homosexual interaction and still raise the interests, so to speak, of a general moviegoing audience? You make it about lesbians and you make it as clever you can. The heart of Kissing Jessica Stein is more about friendship than sex though early in the film it tackles the topic of why girl-girl connections are sexier than guy-guy connections. If you have no tolerance for same sex interactions, look elsewhere. More to the point, the "bonding" scenes work but when combined with the seduction and/or makeout scenes, the movie drags. Only a healthy dose of New York Jewish humor, and almost every character in Kissing Jessica Stein is a Member of the Tribe and a character out of the Sandra Bullock mold keeps the movie working. Of course we've 'fessed up before that Bullock drives this MOT absolutely crazy out of his severely damaged gourd. Your results may vary.

Let's put it this way: IF Cranky (whose social life adds a tenth circle to Dante's Inferno) brought a girl like Jessica Stein (Jennifer Westfeldt) home to meet momma, the old lady would kvell in her orthopedic supports. A copy editor at the New York Tribune newspaper, Stein is much more than plain book smart. Right off the bat you know she doesn't stand a chance in the kill or be killed dating world. Flanked by her mother Judy (Tovah Feldshuh) and Grandma Esther (Esther Wurmfeld) on the Holiest Day of the Jewish Year, Yom Kippur, the older ladies evaluate all the single men of the Congregation as they repent their sins, whether they did 'em or not. While this portion doesn't include the list of truly stomach tuning sins that we've got to give up, anyone outside of the Tribe cannot fail to make the connection to intrusive parents worried about single progeny and their attempts to fix the problem.

It's very funny. But poor Jessica is surrounded by signs of Happiness and Commitment and that gets her down. Her friend and coworker Joan Levine (Jackie Hoffman) is pregnant. Her usually offscreen brother Danny (David Aaron Baker) has just popped the question and presented the ring to his beloved Rachel (Jennifer Carta). Then there's Josh Meyers (Scott Cohen), her boss and one time significant other, who was dumped because he is/was one royal jerk. As for her own life, the awful loneliness of perpetual singlehood looms hard and threatening over Ms. Stein. The only alternative: Dates From Hell. From the writer with a mangled vocabulary to the accountant who splits the bill down to the individual cost per piece of the greens in the salad they shared, it's a generic scene and just as funny as every other DFH sequences you've ever seen. The alternative? The Village Voice. Single New Yorkers all know that perusing and/or using the VV personal ads are a mandatory rite of passage. This film tips that adding a serious quote from any philosopher studied in college is a sure way to attract the upper echelon of readers. It is a quote from Rilke that catches Ms. Stein's ear when Joan reads it out loud. The only problem is that the ad is in the "Women Seeking Women" section. When no one is looking, Jessica answers the ad, curious but not much more.

Her date is Helen Cooper (Heather Juergensen), a bisexual shark of a lady, who has picked the quote aided by pals Martin (Michael Mastro) and Sebastian (Carson Elrod), intent on nailing a strait girl. There's nothing malicious about it. Just like a lot of what passes for the downtown scene, Helen is bored and seeks a challenge. She's not about to let Jessica off the hook but she's not shallow enough to walk after all her passes are rejected. As much as her character softens, Helen is not about to wait forever even as a strong friendship blooms. Jessica knows it. She sets a date to finally make up her mind. Here is where the movie kicks into high gear, not because of anything to do with sex, but because of the insertion of Jessica's mom into the mix and the perpetual problem of those in the closet about trying to hide that fact from everyone in their lives.

That doesn't mean we've tipped the Third Act, unless we have. Kissing Jessica Stein is a very sophisticated, very urban comedy, which means it may not "play" outside of New York, LA and the indie circuit. Speaking solely of the first two acts, Jessica's waffling character coupled with a performance by Juergensen that we found weak, keeps this Kissing Jessica Stein at our indie film ratings level, our trembling knees aside.

On average, a first run movie ticket will run you Nine Bucks. Were Cranky able to set his own price to Kissing Jessica Stein, he would have paid . . .

$4.00

For those who avoided philosophy, or college, like the plague, buy a copy of Bartlett's Familiar Quotations. (our "in short" quote by Rilke from the 16th edition softcover, page 630. heh heh heh.)

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The Cranky Critic website is Copyright © 1995  -  2017  by Chuck Schwartz. Articles by Paul Fischer are Copyright © 1999 - 2006 Paul Fischer. All images, unless otherwise noted, are property of,©, ®, their respective studios and are used by permission. All Rights Reserved. Not to be used or copied for any commercial purpose. Academy Award(s) and Oscar®(s) are registered trademarks and service marks of the Academy of Motion Picture Arts and Sciences.