A film by Charles Herman-Wurmfeld

I hope that this movie does not get dismissed or categorized as that cute lesbian movie because Kissing Jessica Stein is much better than that. Jessica Stein (Jennifer Westfeldt) seems to be channeling Woody Allen (in his Annie Hall days), as a neurotic, Jewish, single woman who is not having much success dating. Feeling depressed about her dating life, she decides to answer a personal ad but this is a female seeking same personal ad and Jessica is not a lesbian.

The woman who placed the ad is Helen Cooper (Heather Jurgensen), who when Jessica tries to get out of the date is able to talk into staying. This begins a friendship that quickly moves into an awkward relationship. Jessica is interested in Helen, but has to move very slowly in becoming physical because of her inhibitions and fears. Kissing Jessica Stein is a romantic comedy that just happens to be about two women rather than a man and a woman.

Kissing Jessica Stein is a charming, witty, romantic comedy and is a rather cute movie. The acting is excellent and Jennifer Westfeldt turns in a better Woody Allen performance than Woody has done in more than a decade, and she is cuter and sweeter than Woody. Jessica s neurosis is toned down, but we do see that her choices have something to do with how her dating life has turned out. But, it is in the relationship between Jessica and Helen that this movie is really strong. The film captures their frustrations and the building of their relationship very well that it feels real and not forced. This is a film about their relationship and because of this (and the performances), it works.