Kissing Jessica Stein (2001)

Directed by: Charles Herman-Wurmfeld


Starring: Jennifer Westfeldt, Heather Juergensen, Scott Cohen

The Main Review: Kissing Jessica Stein was a 2001 film in which a woman, Jessica Stein, decides to stop dating men and try dating a woman. She gets involved with the lovely Helen, who was also, until recently, only engaging in heterosexual relationships. The two of them pair up in what's supposed to be a sweet, quirky romantic comedy about straight girls going gay. Sounds adorable, right?

Yeah, not so much...

All of the men in Jessica's life before meeting Helen were unattractive, unintelligent, jerks and/or already taken. Her mother keeps trying to set Jessica up with other Jewish men that she just doesn't find herself attracted to. There are two conventionally attractive men shown in her life, one of them being her snarky, ex-writer, ex-boyfriend boss (Scott Cohen)  and the other being taken (John Hamm). It just kinda makes sense that she'd try dating in a different group, especially when they put such a charming and non-threatening personal ad in the paper.

There's a lot of middle stuff about painting and dating and being accepting of being gay (I mean, hey, this is a rom-com). What we find is that Helen and Jessica do have sex and, while Jessica isn't really used to it, she thinks it's good. So, Jessica and Helen do fall in love, do engage in physical intimacy and, by what seemed like the end of the movie, go to a wedding together as an open couple.

Of course, at the wedding, her jerk boss shows up a new, better man. He's started to do his bohemian writing thing, he offers her his coat when she's cold, and, being the only person at this point who doesn't know about Jessica and Helen, confesses his deep, romantic feelings to her. He's attractive, he's intelligent, he's nice (now) and he's very available. We can all see that Jessica is tempted, but she refuses his dinner invitation because she's with Helen. So, for that moment, the audience feels satisfied in Jessica and Helen's relationship and love for one another.

Here's Where It Gets Spoilerific: The movie doesn't end there. We see a cute little montage of Helen and Jessica moving in together and being a couple. Then, there are a few scenes of their relationship a few more months in. It appears that Jessica is avoiding - whether purposefully or not - having sex with Helen. In the very end, Helen breaks up with Jessica for not wanting to have more sex with her. Jessica is obviously distressed and tries to get Helen to stay, because, you know, she loves her.

Flash forward another few months, Jessica goes to a bookstore and finds her old boss there. They've, by this point, both quit their jobs and are working on their artistic careers. Of course, the two of them decide to see each other. Then, Jessica goes to have lunch with Helen - the two of them now just best friends. The movie ends and I leave with a displeased feeling in my stomach.

Scenes To Watch Out For: Helen trying to talk to Jessica about their sex life in public and Jessica trying to get her to stop. While Helen sees it as Jessica just not being open about their relationship, I see it as a basic desire to have privacy. But, obviously, wanting to have some privacy when it comes to sex makes you uptight.

The scene where Jessica is pleading through tears with Helen, asking her not to leave, saying she really loves her. And Helen saying they're just roommates.

Anything Else: For Christ's sake, this is supposed to be a rom-com. I was pretty sure that meant fun and light, with a happy ending. Maybe it's just my looser view of sexuality, but I was pretty sure that these two girls loved each other. The movie didn't go too far into their sex life, which is fine. However, it does mean that we have no idea what these two women tried when it comes to sex. I can't tell exactly how much effort they'd put in before Helen threw in the towel.

Also, I don't know if Jessica Stein being heterosexual in the end makes the movie sell better to the public. I think that might be why. The movie is fairly explicit - or at least more explicit - with showing heterosexual sex then the lesbian sex. In fact, the most lesbian action we see is some timid kissing between Jessica and Helen. However, Helen and one of her boyfriends are shown to be very intimate at times. I guess it's to give the heterosexual female viewers something they like, while also giving them the sense of being "adventurous" and "open-minded" because they watched a movie about "lesbians."