Romancefest 2016: Kissing Jessica Stein

I was pretty sure I rented Charles Herman Wurmfeld's 2001 flick KISSING JESSICA STEIN back in college but I wanted to check it out again. And guess what? I totally couldn't remember any of it. So maybe I didn't rent it back in college. Who knows?

This American indie flick was written by its two stars, Jennifer Westfeldt and Heather Juergensen. Westfeldt stars as the titular Jessica who is striking out with a string of shitty dates with hetero dudes and currently works as a copy editor under her ex (Scott Cohen).

Juergensen co-stars as a more sex positive chick who has a variety of different booty calls ready at any time based on her mood, but is getting bored. Maybe it's time to date a chick? With the help of some friends she places a personal ad that quotes Rilke, and this catches Westfeldt's eye. All the dudes she's trying to date suck, so why not try a chick, Westfeldt thinks.

So, here we have two ostensibly straight chicks trying out lesbianism "just in case." In some ways this is kind of a dated premise -- even though 2001 is not that long ago, gay love stories had to be couched in straightness in order to have any chance at mainstream acceptability. I'm not saying in this day and age the whole gay thing has been totally solved and accepted, but it has been way more than it was back in 2001, and this movie is an artifact of that: it's okay to have a lesbian love story as long as you assure everyone that these chicks are REALLY straight. I guess I should stop saying "chicks."

Anyway, it's all awkward and stuff at first, but then they start to get into it, and then it's a question of how much Westfeldt can loosen up (she's kinda uptight) and how much Juergensen can commit.

Despite its somewhat dated premise, KISSING JESSICA STEIN comes to a fairly realistic and satisfying ending. Stop here if you don't want spoilers, but it's refreshing how the two women's relationship works out, then fails, and then they're still able to be friends. Juergensen goes on to try more relationships with women and Westfeldt has to admit to herself that maybe her future lies in dudes after all. But what they do find out is that they do love each other in a platonic way and want to keep on doing that. And that's nice, for a change.

I'd have to turn in my MAD MEN fan club card if I didn't mention young Jon Hamm has a quick cameo here, too.