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Kissing Jessica Stein is a pleasant little surprise of a movie that provides a fresh take on an old theme: Loneliness and dating in the big city.

Studs, Duds, and Rosebuds

Jessica Stein (Jennifer Westfeldt, TV’s Two Guys, a Girl and a Pizza Place) is a journalist for the New York Tribune. She’s terminally cute and single in the Big Apple.

After a string of dates with guys who are too anal, too shallow, too self-absorbed, or too intense, it’s clear Jessica’s trying, but she just can’t connect with the right guy. And having a brother who’s getting married and a Jewish mother eager to see her walk down the aisle doesn’t make things any easier for our heroine.

Even her editor and former college friend, Josh Meyers (Scott Cohen, Private Parts), takes her to task for her dating situation. During a dinner party, he makes the observation that Jessica’s biggest problem is Jessica herself because she is simply not open to the possibilities right in front of her.

Of course, Josh’s comments are really referring to their own relationship. But, with his comments egging her on, Jessica decides to take the plunge and reply to a personals ad that was the topic of previous office banter.

It’s not a single white male seeking a single white female kind of ad. It’s an enticing ad placed by a single white female seeking same.

A firecracker of a wild child, Helen Cooper (Heather Juergensen, The Afterlife of Grandpa) placed the ad because she’s looking for the next natural high. Helen manages an art gallery and a string of men, sometimes satisfying both at the same time. Promiscuous and adventurous, she wants to experiment with playing for the other team. To her advantage, she has a couple homosexual male companions giving her some humorous pointers and advice.

Such a vixen is the perfect foil for the sweet, innocent charms of Jessica, a girl who worries about being a Jewish Sandra Dee.

Shine Like Stars

Kissing Jessica Stein is an independent film picked up by Fox’s “art house” distributor, Searchlight. It has no big names in front of or behind the camera, which makes it all the more qualified to be honest and it is full of on-target observations about single life, dating, and loneliness in the new millennium.

This film is far more witty and smarter than Ed Burns’ star-studded and pretentious Sidewalks of New York, a dreary excuse for a film that tried to cover some of the same ground, but failed miserably both creatively and at the box office. Kissing Jessica Stein is a very small film, but it deserves attention.

In his first stint as a feature film director, Charles Herman-Wurmfeld (TV’s The Facts of Life Reunion) provides a unique take on the subject matter that combines wit, drama, and a very clever use of music.

Westfeldt and Juergensen are triple threats by co-starring, co-writing, and co-producing the film. Together, this dynamic duo offers hope that the future of cinema might not be Britney Spears after all.

As writers, they provide dialogue that sounds natural. As actresses, they deliver performances that are fresh and engaging.

Welcome to the Jungle

Beyond being about relationships and loneliness, Kissing Jessica Stein also has a theme about the importance of finding what makes you happy and going for it. It’s the same message Joseph Campbell offered: Follow your bliss.

The story’s threads weave together a gentle and oddly comforting tapestry. Its message: You’re not alone being single, but there’s the bigger picture to look at, too.

Near the film’s end, there’s a nice scene that captures the simple pleasures of rekindling old friendships during a random run-in at a bookstore. That scene, in a fashion, ties things together and follows the old maxim, “Ya never know…”

Another aspect that sets this little film apart is its character development. There is an arc to the characters’ lives and by the film’s end, the characters have grown, changed, moved on, and taken steps to make themselves happy.

The most dramatic changes revolve around Jessica herself, and Westfeldt is to be credited for pulling it all off so naturally. She’s not the same woman she was at the beginning, and the changes are thoroughly believable.

Refreshingly, it is all done without being preachy or judgmental and the characters openly acknowledge that no one lifestyle is right for everybody. Jessica and Helen’s alternate lifestyle experiment is merely one facet of the movie, but it’s the one that will get the most attention. That’s unfortunate because this movie is really not a “lesbian movie.” There is much more than that going on here.

Granted, the movie meanders and feels longer than its 94-minute running time, but it still leaves a positive impression and a quiet sense of optimism. It’s the kind of material almost anybody can relate to who’s been told, “You could do better” and/or “You’re being too picky.”