A worthy addition to the "love theory" subgenre (in the tradition of Swingers, Chasing Amy, Annie Hall, and When Harry Met Sally), Kissing Jessica Stein's combination of true-to-life characterisations, sharp dialogue and considerable charm delivers the best Hollywood romantic comedy in quite some time.
A comedic meditation on the fluidity of sexuality (not to mention Jewishness, New York, and the oft-ignored yuppie/hipster divide), Kissing Jessica Stein stars Jennifer Westfeldt in the title role as a neurotic New York newspaper editor looking for love and constantly coming up short. So in a fit of desperation, she answers a personal ad from free-spirited bisexual artist Helen (Heather Juergensen), and to her surprise (though not to the audience's) the two fall in love.
The two actresses are incredibly charming in the roles, and though the film is less frank about sexuality than some of its predecessors (there's more talk than action), the script perfectly captures the naiveté of a new couple in a new situation. The film is at its sharpest when depicting the actresses' whip-smart dialogue, especially in the date scenes. You'll also be treated to some of best Manhattan cinematography in recent memory.
With one glaring exception, Kissing Jessica Stein also deals astutely with the issue of Jewishness, especially through the characters of Jessica's mother (the veteran stage actress Tovah Feldshuh) and her boss/bitter ex-boyfriend (Scott Cohen). Watch out for the shabbat dinner party scene for some fine work by Feldshuh, skillfully transcending the type of clichés usually inherent in such Jewish-mama roles.
The film doesn't shy away from addressing the sharp differences between the social lives of careerist yuppie Jessica and free-spirited bohemian Helen. While often dealt with on screen in frames of class conflict, this more lifestyle-based divide is rarely addressed as honestly or comically as in this film.
The only place where the movie really steps wrongly is in its final act where credibility flies out the window to make way for an easy ending. Considering all of its charm and lovability, had Jessica Stein made room for five more minutes to tie up the loose threads, it would come as close as possible to the perfect romantic comedy.
Kissing Jessica Stein comes from the Swingers/Good Will Hunting formula in that it was conceived by two struggling actors who wrote it with the intention of starring in it, and succeeded. How Westfeldt and Juergensen will fare in other roles remains to be seen, but their debut film is impressive enough that it will likely not be soon forgotten by anyone who sees it.