Kissing Jessica Stein is the light, breezy romantic comedy that all movie makers hope to make but often miss somehow. The main difference here is that instead of a man and a woman, the two people possibly falling in love are two women. Thankfully, Kissing Jessica Stein does not fall into the typical pitfalls of conventional romantic comedy, and also does not fall into the constant whining of the gay and lesbian movie subgenre. If everything seems acted and timed to perfection, it is because it is. Jennifer Westfeldt and Heather Juergensen, the two writers and stars, performed this show on stage before this film. There, they pre-ironed out all the kinks, and make an easy transition to the big screen.

It's not that Jessica Stein (Westfeldt) is a lesbian per se. She is single, neurotic, Jewish woman nearing thirty and desparate for a smart, funny man. Either all her dates (amusing portrayed in succession) are horrific, or she is much too picky. She wants a handsome, smart man who knows how to use grammar properly. Her mother (Tovah Feldshuh, Happy Accidents, The Corruptor), believes it is the latter, and continually, and unsuccessfully, tries to set her up with men. So when a personal ad with a quote from her favorite author catches her eye, she is immediately intrigued. Even moreso after she realizes it is an ad from a woman, seeking a woman. Helen Cooper (Juergensen) is not a lesbian either, but is trying something new. The sparks don't exactly fly between them, but they do find that they like each other's company.

Jessica plays the same, neurotic Jewish person that seems to be the stereotype. But Westfeldt does such a fresh and amusing job that it is forgiveable. She's an editor under Josh Meyers (Scott Cohen, King of the Jungle, Silent Witness), an ex-boyfriend from college. In college, both had their own dreams. Josh wanted to be a writer, and Jessica an artist. Reality intruded and they pushed their dreams aside for duller careers. Helen works at an art gallery, and her relationship with Jessica sparks a renewed interest in her old dreams. Jessica is happy, and everybody around her sees this, especially Josh. He finds himself slowly drawn to her again.

There is nothing really new in Kissing Jessica Stein, aside from the same gender relationship. This gives director Charles Herman-Wurmfeld (Fanci's Persuasion) a new spin on relationships. Jessica and Heather's basic situation has nothing to do with gender, it has more to do with wanting something new in a relationship.