Kissing Jessica Stein

“She wanted to be with someone a little more…gay, I guess is the thing.”

Kissing Jessica Stein is about a straight lady who dates a girl, dreads having sex with her, and then dumps her for her ex-boyfriend, but I still pretty much liked it. Helen decides to try dating women, and places an ad in the paper, which Jessica answers on a lark. The part of the movie dealing with Jessica’s anxiety about anyone finding out she’s with Helen, and overcoming her initial repulsion to lesbian sex, stressed me out a lot. I mean, I don’t have the greatest taste in girlfriends, but if you have to actively work to overcome your partner’s disgust with the idea of touching you, you could maybe do just a little bit better. Especially if you look like Helen.

But Jessica’s many neuroses, and her panic about bisexuality, are presented as symptoms of her perfectionism and anxiety about life in general. She’s picky about everything, and decides to go out with Helen because she’s ruled out the entire male gender, and then realizes that the emotional fulfillment she and Helen share isn’t enough to make up for the lack of sex Helen wants. What Jessica wants is a best friend to cuddle with and keep her from being lonely, and Helen wants to be in love.

Helen’s bisexuality is treated with surprising decency: she goes out with Jessica as an experiment, and decides she likes women as well as men, without any of the hand-wringing and self-flagellation Jessica goes through. She decides what she wants and then gets on with it, and at the end of the film, when she and Jessica have broken up, is still dating both men and women. She and her two gay male friends have a series of conversations that seem to be intended to answer lesbian complaints about the plot of the movie, including one where her friend compares having a lesbian relationship on a whim to wearing blackface, to which Helen responds, “Oh, come on, that’s a bad comparison. People are born black,” and her friend says, “Exactly!” The movie seems to be suggesting that sexual orientation is less set than many people are comfortable with, including, I guess, me—maybe because that scenario of your girlfriend dating you on a whim and then leaving you for a boy because it turns out she doesn’t like having sex with you, but really likes the emotional support, is terrifying. Which is the source of a lot of biphobia, and wrong, and not so much a problem with bisexuality as people making mistakes with what they want, but Jessica Stein is kind of a nightmare scenario.

There are a lot of things I really liked about Kissing Jessica Stein. The acting is great, and the dialogue is witty. Jessica’s relationship with her family is lovely. This scene with her mother, right after Helen dumps her for not coming out, has the most emotional depth in the entire film:

Mom: You okay?

Jessica: Uh, I don’t know. No.

Mom: What is it, Jess?

Jessica: It’s just sometimes I tihnk I’m gonna be alone forever…You can jump in any time.

Mom: You’re my love, you know that? My beloved. But sometimes I worry for you.

Jessica: I worry for me too.

Mom: Sweetheart. I will never forget when you were in the fifth grade, and you were so excited when you got the lead in the play. Do you remember that? Really Rosie.

Jessica: Really Rosie. Yeah, I remember.

Mom: And you came home after the first day of rehearsal, and you turned to me, and you said, ‘Mommy, I’m not gonna do it. I quit.’ Just like that. I turned to you and I said, ‘Jessie, Jessie my love, why?’ And you said, ‘Because my costar isn’t good enough. And if my costar isn’t good enough, then the play won’t be good enough. And I don’t want to be part of any play that isn’t good enough.’ And I thought to myself, ‘Oy. This child will suffer. How this child will suffer.’ And then they gave it to the meskite with the glasses.

Jessica: Tess Greenblatt.

Mom: Right.

Jessica: God, she was terrible.

Mom: Right. And you would have been great. And you didn’t get to do it. You had to sit there and watch terrible Tess do it with that guy you thought wasn’t good enough, who was actually quite excellent, wasn’t he? And you know? I always thought that you would have been so much happier doing that play, even if it was just okay. Even if it was great, just not the best ever. And maybe, just maybe, it would have been the best ever. You never know. Jessie?

Jessica: Yeah?

Mom: I think she’s a very nice girl.

If all the relationships were this well-crafted, I’d be thrilled with it, but the movie is unfortunately poorly paced an the characters aren’t terribly fleshed out. We cover huge spans of time in minutes, jumping from Helen being embraced by Jessica’s family to them moving in together to Helen complaining that they never have sex to them breaking up because of lack of said sex. It’s a mess, and we don’t really see why Helen is attracted to Jessica in the first place, or why Jessica and her boyfriend would make a good couple, which, for me, makes it a bit of a failure as a romantic comedy.