The Unicorn Scale: Kissing Jessica Stein

Hey there, Unicorn readers! I do so love our times together. What a joy to bring bi characters in shows/films to the spotlight, and also look back and see how far we have come in queer representation. With that in mind, let’s take a look back at one of the controversial LGBTI additions to mainstream cinema, the 2001 independent darling Kissing Jessica Stein.

Before I get in too deep to this world of femme queerness and blended lipsticks, I should throw down a few disclaimers. First and foremost, I will need to put up a SPOILER ALERT for plot points in this article. I should also put out a TRIGGER WARNING: biphobic language and racially insensitive content. Finally, as always, if you are new around these parts or just want a refresher on the Unicorn metric, you can always head over and review how it all works before we dive in.

Kissing Jessica Stein follows the life of the eponymous New York painter (Jennifer Westfeldt), a perfectionist terrified of taking risks in almost anything but her painting. Working as a copywriter and slogging through a sea of unsuitable male dates, Jessica decides to answer a classified ad (remember those?) in the “women seeking women” of the newspaper she works on. The ad, sporting a Rilke quote and asking for “friendship and maybe more”, comes from the sexy Heather (Heather Juergensen), a manager at a contemporary art gallery.

What I Liked:

There are some good elements to consider here. KJS was one of the first main entries into the modern film pantheon of a woman exploring her bisexuality. And doing so in a romantic comedy lends the subject levity that makes it more palatable to the mainstream (and mostly straight) audiences.

I also tried to approach this piece, and Jessica’s journey, with some empathy. Though she and I are wildly different characters, in 2001 exploring a same-sex attractions was new, and feeling and exploring queerness was even newer — and felt risky and scary. Westfeldt, both writer and producer on the film, gives a lovely performance depicting the delicate breathiness and broad fears of coming out while still figuring herself out. By comparison, Heather is a bi woman completely comfortable in her own skin and sexuality — something we still struggle to see in 2019.

What is lovely is that most of the main players, once they find out Jessica is dating a woman, are accepting and positive. One gay friend who encouraged Heather to go on the initial date declared “an orgasm is an orgasm”, dismissing biphobia in a breath. And in the most surprising and touching scene, Jessica’s mother Judy (Tovah Feldshuh) tells a simple but heartrending story on why Jessica has found the right person. She gives the kind of speech many queer kids from my generation wish they had gotten from their parents – in the same vein as the final speech in Call Me By Your Name.

Oh, and there is loads of the female gaze. And the film passes the Bechdel Test and Mako Mori test multiple times. That’s important to consider, considering its time and place in film.

Ooh, I kind of buried a lead here — baby Jon Hamm is in the film as well. And he’s precious.

What I Didn't Like:

As I said before, Kissing Jessica Stein is a good way to see how far we have come in terms of bi representation and bi acceptance in modern films and media. And for its time, it was groundbreaking and made palatable with an amusing rom-com framework. However, Kissing comes with its own issues of bi erasure — which is hard to swallow considering the film’s entire premise. Is it as bad as that one episode of Sex and the City? No, but …. well, let’s take a look.

First and foremost, for a movie that centers on a questioning woman and her bi lover, the script sure seems to have a problem using the word “bisexual”. The only time (in my memory) the word even comes up is when one of Heather’s gay friends uses the term “bi-curious”. But that. is. it. Heather discusses her bi past, and obviously Jessica is exploring a same-sex attraction and relationship with Heather for the first time. But all other same-sex attractions with women are referred to (or joked about) as lesbian. One of Heather’s gay friends even rebukes Heather’s forays into dating women, making a terrible analogy comparing it to blackface. Sadly, this reflects a lot of the rejection many bis experienced (and still do) from much of the LGBTI community, and though one of Heather’s friends comes to her defense, the whole scene leaves a bitter taste in the mouth.

There is also the argument in queer circles that this story falls into the “experimenting” genre, since ultimately Heather is the only woman Jessica dates (to our knowledge). “Queer as conflict” is a subject of hot debate in non-straight literary circles, and they will not be satisfied with what they find here. To point, in the final scene, Jessica either misses or ignores a flirtation from a bookstore clerk but happily strikes up a conversation with her former boss/boyfriend, Josh (Scott Cohen).

While much of the arcs for both Jessica and Heather are relatable, they are easy to dismiss as part of the bis-in-film stereotypes. Both actresses are heterosexual in real life, for one. Heather could be categorized as an overly sexual character, since in multiple scenes she is banging one sexual partner while thinking about or talking to a different lover. Jessica’s hesitation and internalized biphobia also doesn’t seem to get completely resolved. And when Heather breaks up with Jessica because of a lack of sex, there isn’t much discussion about it. 

While I agree with Heather that Jessica was more interested in the idea of Heather than her in reality, this could have been a good moment to discuss opening the relationship, putting together a sex schedule, or seeing if the sexual drought is a blip or a pattern. But this quick dismissal can make it seem like all Heather cared about was sex — a bi stereotype I’m tired of seeing perpetuated.

Also, despite being the other romantic lead, Heather doesn’t have much else going on in her life. She has a cool job as an art gallery manager, but we don’t see much about that other than fun background dressing for her to complain about Jessica (or maybe to get in a quickie in her office). She doesn’t have much of an arc other than her romantic ties with Jessica. Not only that, her support system of the gay couple is stale and tired, even by 2001 standards. These catty friends don’t seem to exist except as a soundboard for Heather. They hit the “gay best friend” trope in Isn’t It Romantic almost to a tee.

The Rating:

Like a good decade of queer reviewers, I am very mixed about Kissing Jessica Stein. It had its place in time, the characters are generally positive and replete with witty dialogue, but it hits a whole lot of tropes. There are heartwarming moments and even groundbreaking ones, but ultimately I felt a little hollow at the end. I’m glad it exists because it paved the way for nuanced representation. And nobody died. Yay? This may be “see and judge for yourself” fare. But if you need more nuanced work as a palate cleanser, I cannot recommend Good Trouble enough.