Kissing Jessica Stein (2001) is an American independent romantic comedy written, produced by, and starring Jen Westfeldt as the title character. The film focuses on Jessica, a woman who’s a daring painter but risk-averse in her personal life. After too many bad dates with men, she goes out on a limb by answering a “women seeking women” ad in the newspaper where she works. Enter Heather (Heather Juergensen), a sexy and confident bi woman who works at a contemporary art gallery.
The sweet and heartfelt film has a lot going for the two bi leads. Most of the other characters are accepting of Heather and Jessica’s relationship and bisexuality — including Jessica’s mother, who gives a touching monologue about acceptance. The story shows a strong female perspective and avoids nearly every tired sexist movie trope. In particular, Heather’s comfort with and confidence about her bisexuality is very ahead of its time (at least as far as cinematic representation).
However, for a movie about two bi women, it doesn’t use the term “bi” much — in fact, the closest we get is a single usage of the term “bi-curious.” At times, Heather and Jessica also display some bi stereotypes, such as a deceptive scene where Heather is having sex with one partner while talking to another lover, an act that clashes with the fact that she doesn’t have much else going on in her life other than her relationship with Jessica. Ultimately, Heather is not a fully drawn, three-dimensional character with hopes, dreams, and fears, but rather more of a (sometimes) patient and tropey queer guide along Jessica’s path of self-discovery.
One saving grace is that, at least during press interviews, Juergensen was not afraid to call a spade a spade. From an interview with Spinning Image:
I enjoyed playing the role of Helen, I enjoyed exploring the bisexual nature of that character.
While Kissing was helpful and groundbreaking in its era, as far as bi representation, it is best to view it as a stepping stone towards more fleshed-out bi stories that came along in the 2000s and 2010s. Even so, Kissing Jessica Stein remains a charming film worth watching.