Kissing Jessica Stein

Being a struggling actor in Hollywood is a lot like dating in the big city. You have to have a thick skin in order to deal with the constant amount of rejection, and you may have to go on a lot--and I mean a lot--of bad dates before you finally meet your perfect match. That is, if you ever do.

Oh, I'm sorry. Was that too bitter? What can I say, I guess I speak from experience.

Anyway, after being in the company of struggling actors for years, Jennifer Westfeldt and Heather Juergensen have finally emerged with two perfect roles to match their talents. And how did they manage this rare feat? By doing what Matt Damon and Ben Affleck did with 1997's "Good Will Hunting"-- they wrote the parts for themselves. While the resulting film doesn't have a shot at duplicating "Hunting's" $138 million box office (and Oscar-winning) success, "Kissing Jessica Stein" comes close in other ways by being a charming, funny, and engaging romantic comedy--with a twist.

Why is it so hard to find Mr. Right in a city with more than 8 million people? That's the question that hopelessly single New Yorker Jessica Stein (Jennifer Westfeldt) can't seem to answer. After a string of horrible blind dates, the fed-up copy editor answers a personal ad from...Helen (Heather Juergensen), a bisexual art gallery assistant. Helen is everything that the uptight, neurotic Jessica is not--she's aggressive, free-spirited, and very much in touch with her sexual side. Their initial meet-and-greet is understandably awkward, but that changes when they make a strong emotional connection (over lipstick, no less!).

Jessica decides to give the relationship a whirl, but she soon realizes that she is in over her head with some pretty complex issues. Among them: Does dating another woman make her a lesbian? Should she keep the relationship private? What will her friends think? What about her family? How long will Helen have to wait in the shadows before Jessica finally decides to make the relationship public?

"Kissing Jessica Stein" deals with gay issues in a broad and commercially appealing way so that mainstream moviegoers will be able to embrace it. After all, given the difficulty of meeting the right person these days, who can blame Jessica for contemplating what it might be like to bat for the same team? As for whether or not that defines her sexual orientation, that can't be answered without giving away too much of the plot. Suffice to say, moviegoers will have plenty to talk about long after the credits roll.

By adapting their own 1997 play "Lipschtick," Jennifer Westfeldt and Heather Juergensen have written appealing, true-to-life characters for themselves while still leaving plenty of room for equally strong supporting roles. Tovah Feldshuh brings loving, sensitive support to her role as Jessica's overbearing mother, and Scott Cohen brings jealous, confrontational realism to Jessica's still interested ex-boyfriend--a matter further complicated by the fact that they work together (and he's her boss!).

Try and imagine what would happen if Woody Allen directed an episode of HBO's "Sex and the City," and there your have "Kissing Jessica Stein." The film is not without its flaws--there are some noticeable stereotypes and the ending feels too rushed--but Westfeldt and Juergensen have done what few before them have been able to do: write for themselves and entertain others in the process. If your thick skin is starting to wear thin after seeing too many bad Hollywood movies, then "Kissing Jessica Stein" should fit the bill as the perfect cinematic match that you've been looking for.

There, now, that wasn't too bitter, was it?