Ten Years Later: “Kissing Jessica Stein”

Jessica Stein, unlucky in love. (Has there ever been a romantic comedy where the protagonist is super lucky in love, by the way?)

I came across Kissing Jessica Stein while researching The Hammer for a piece that was published a few weeks back. The Hammer stars Heather Juergensen, an actress I’d not seen before. Looking at her short filmography I noticed this picture and, given it was well received by critics, decided it was worth a look. It was a fortunate decision. I expected a good romantic comedy, but I got more; I got an excellent film, an indie picture shot on location in New York that blows most other rom-coms out of the water. It doesn’t have big talent, and it doesn’t have obscenely high production values, and yet it leapfrogs most of what we’ve seen from this genre over the past decade.

Jennifer Westfeldt and Heather Juergensen star opposite each other. Westfeldt stars as the film’s titular character, a Jewish copyrighter in her late twenties who is unlucky in love, while Juergensen plays Helen Cooper, a bisexual art gallery manager. In an attempt to find a new female lover, Helen runs a personal ad in a newspaper which Jessica happens across. Ms. Stein’s interested is piqued, despite the fact she’s very straight. Given her recent frustrations over dating men, she decides to answer, and so they strike up a relationship. It proceeds at a glacial pace—Jessica, being heterosexual, turns out to be utterly frigid when it comes to the meat of the relationship—but eventually things heat up. The only thing that remains to be seen is if it will last, and if Jessica will forgo men indefinitely.

Jon Hamm makes one of his first acting appearances here. Incidentally, his voice is disconcertingly soft—he's not the deep Don Draper yet.

I’m probably not in the target demographic for romantic comedies, and indeed there aren’t many that appeal to me, but Kissing Jessica Stein hits the mark as squarely as a film could. It is precisely what you would hope it is: genuinely funny (which all too many romantic comedies are not), as well as charming and, at times, heartwarming. Watching it, one can’t shake the feeling that Kissing Jessica Stein is essentially a thinly-veiled homage to Woody Allen. After all, this may be why I enjoyed it—I am a Woody Allen fan, and for me his romantic comedies represent the genre’s best. There’s no shame in copying from the master, if the master is indeed as good as he is chalked up to be (and, of course, Allen is). So, perhaps predictably, Kissing Jessica Stein is very New York and very Jewish, and it has an ample dose of neurosis as well. It essentially hits all the checkboxes on the Allen formula list. As it happens, Westfeldt and Juergensen (who wrote the film themselves) do a better job of it than Allen himself did around that time.

Perhaps its greatest strength is its convincing portrayal of life’s minutiae. That’s part and parcel of making a film on a shoestring: one doesn’t have the time to indulge in aggrandized narrative hooks, and Kissing Jessica Stein doesn’t. It feels very honest as a result—we discussed honesty in rom-coms in our look back at Annie Hall—and that’s crucial to this picture’s success. There’s no runaway dumpster that threatens to flatten our heroine (see The Wedding Planner), no man who has the ability to read women’s thoughts after accidentally electrocuting himself (What Women Want). It’s so well written that we don’t notice the plainness of its subject matter, and the fact that everything is treated on the level.

The film takes itself as seriously as a rom-com can, and the acting is good across the board.

For instance, there are no caricatures here; Helen’s gay friends are suitably extravagant but not on the nose (as other films would have made them), and Helen is more ordinary and secure than Jessica is (other films might have made her harebrained just because she’s bisexual). Add to that the fact that time has made some aspects of the film amusingly quaint, and it all ends up coming off as charming. Jessica doesn’t have an email address to hand out to people because she’s not “into computers” (this was filmed in 2001, after all), and Helen puts her personal ad in the newspaper. Newspaper? What’s that? It’s a flashback, and I’m nostalgic. Westfeldt and Juergensen didn’t plan for the film to have this effect, but that’s what time does. Time can unfriendly, but it doesn’t cast a shadow here. If anything, aging has been beneficial to this picture.

All good romantic comedies shift in tone towards the end of the picture, typically in the last act. This is something I’ve only begun to appreciate as of late. A good rom-com will have the ‘comedy’ part disappear perhaps for about ten or twenty minutes, and it will then reemerge for the film’s last few scenes. This is where the story typically peaks. The narrative is better served if the audience isn’t being peppered with jokes; the narrative must be allowed to breathe. Jokes tend to marginalize the actual content of the story. While we spend time thinking about how clever the set-up was, or about the actor’s snappy delivery, we end up overlooking what’s actually going on. That, of course, is less than ideal, and so the jokes are quietly phased out. This is true across the board. The final act in Woody Allen’s Manhattan is glum; the same in Annie Hall. As Kissing Jessica Stein goes on, the jokes slowly recede into the background and the film becomes increasingly somber. Towards the end of the picture, Jessica’s conservative mother has a heart-to-heart with her daughter where she reveals she knows that her daughter is gay and that she doesn’t have a problem with it. It is an incredibly heartwarming scene—featuring some great acting by Tovah Feldshuh, playing Jessica’s mother—that is only impactful because it comes at an emotional down-point in the film.

All good romantic comedies turn somber toward the end.

It wouldn’t play if the scene was sandwiched between some comedic back-and-forth. Like other good romantic comedies, this is where Kissing Jessica Stein finds success: it balances its lighthearted side with a story that actually has some consequence. In fact, I suspect that anybody who can relate with either of the two leads might even find the film to be impactful, to resonate with them. That’s a powerful quality for a film like this to have. It doesn’t have to be throwaway; it can have weight, it can have substance. People are praising the recently debuted TV series Girls for the same reason: in part because it’s not vacuous like the many that have come before it. And that’s not a totally facile comparison to draw, either—fans of Girls will find something to like in Kissing Jessica Stein.

Kissing Jessica Stein is respectable. That is a simple statement, but it’s an important one, at least from the perspective of a person that isn’t immediately disposed to romantic comedies (in this case, me). So many rom-coms aren’t that—either they have convoluted storylines, or the acting or directing is atrocious, or there’s some kind of bad characterization that makes you want to cringe. Is it a surprise that the best romantic comedies are the humble ones? And why is that? Is it that they don’t sell compared to their more bombastic, inane counterparts? If so, that’s terribly unfortunate—and it can’t be good for the genre. One of a handful of reasons why the Western genre collapsed was because every film being released was essentially the same story, the same cookie-cutter narrative played out over millions of feet of film. That almost happened to the science fiction genre when it experienced a small decline around the turn of the millennium (it has since rebounded, evidently). One would presume that rom-coms make for slightly bigger business, so such a wane might not be imaginable. But it’s not too hard to fix it, to get it right— Kissing Jessica Stein is evidence of that. The genre can be better than what it is right now. Why not make it so?