On the leading edge of romantic comedy, the fresh, frank and melodiously funny "Kissing Jessica Stein" discovers a novel new avenue to stroll down with the genre's reliable old friend, the romantically frustrated New York neurotic.
Nondescriptly pretty, entertainingly insecure copy editor Jessica Stein (Jennifer Westfeldt) has had it up to her 30-year-old eyeballs with bad dates and dysfunctional relationships -- and we can see why in a quick and comical montage of the men with whom she's been fixed up. She also can't take any more of her busybody Jewish mother (Tovah Feldshuh) pointing out eligible men every week at temple while her near-senile grandma points out all their flaws ("The man has no chin!").
So Jessica goes out on a limb. While reading the personal ads for laughs with her scene-stealing best friend (Jackie Hoffman, a wonderfully waggish cross between Cloris Leachman and Annie Lebowitz), she comes across one that genuinely piques her interest with a quote from a her favorite author. The ad is under "Women Seeking Women," but at this point, she figures, what the hell?
Of course, when she comes face to face with her date, straight-laced Jessica gets cold feet. But chic, slinky art gallery manager Helen (Heather Juergensen) slowly reels her in. They bond over lipstick brands and the fact that, as it turns out, neither one of them have been with another woman before. Almost instantly they're friendly enough to enjoy arguing over Jessica's insistence that she need not try something (like, say, lesbian sex) to know if she'd like it or not.
"You know how you'll react to everything?" Helen balks. "Yes," Jessica replies firmly. Then Helen plants a big, wet, French kiss on her and leaves Jessica flabbergasted.
Sweetly comical, romantic and sexual misadventures soon follow as nervous Jessica and sexually adventurous Helen negotiate how far they'll go on a date-by-date basis. Helen pulls the yawn-and-stretch move while playing a little Barry White mood music, and gets a startled response. Later Jessica interrupts a kiss to inquire, "Uh, is this with tongues?" Afterwards she high-fives Helen and cheers, "That was pretty good!"
As their relationship develops as girl-friends and girlfriends, complications arise with family, secrecy and sex that often evolve into moments of tender sincerity without ever forgetting the movie is first and foremost a comedy. They also face confusion over who pays for cab rides and who opens doors for whom.
Driven by well-developed characters that are easy to fall in love with as they fall for each other, "Kissing Jessica Stein" is popping with personality, amusing awkwardness and idiosyncratic, naturally chatty one-liners. The script was honed over several years by co-stars Westfeldt and Juergensen, who adapted it from their short-lived but buzz-generating off-off-Broadway play of dating scene vignettes entitled "Lipschtick."
The film has several elements in common with several other romantic comedies. The montage of bad dates and a running gag of weird phone messages from Helen's personal ad responders are very similar to 1998's sardonic indie sudser "Next Stop Wonderland." The pretty, harried, neurotic New Yorker who nit-picks men's flaws has certainly become something of an archetype. But the bi-curious twist really breathes new life into the more pedestrian elements, and in the last act "Jessica Stein" definitely veers off the beaten path to explore the entanglements of long-term relationships. Even the picture's stock characters (Jewish mom, bitter ex-boyfriend) become far more complex and interesting than they seem at first.
I've already seen this movie twice -- the second time to take my girlfriend, because gay or straight, "Kissing Jessica Stein" is one of the greatest date movies in years.