As frustrating as it can be to watch America slowly roll back LGBTQ rights, even acceptance, films like 2001’s Kissing Jessica Stein remind us of how much progress we’ve made since people failed to comprehend a concept like bisexuality. Well, let’s not get too ahead of ourselves. Many people still don’t understand bisexuality, but at least for the past few decades, they’ve been trying to wrap their heads around the often-ambiguous nature of sexuality.

 Jessica Stein (Jennifer Westfeldt) is a copywriter for a New York newspaper. The only unpartnered woman in her social group, Jessica feels the arbitrary pressure of the clock running out on her love life, complete with all the double standards that women are subjected to. A string of dates with unpleasant men (featuring early-career appearances from Jon Hamm, Michael Showalter, and Kevin Sussman) Her mother Judy (Tovah Feldshuh) certainly isn’t helping things either, desperate for her to marry a nice Jewish boy, her eyes set on Josh (Scott Cohen), her boss at the paper in a pre-#MeToo environment.

Jessica is drawn to an ad in the personals section of the newspaper (analog dating apps, for anyone reading who’s never picked up a paper), even after she learned that it came from the “Women Seeking Women” portion. Jessica goes out on a date with Helen (Heather Juergensen), awkwardly dipping her toes into the waters of sapphos. Helen is confident, determined, and patient, no stranger to the turmoil that often accompanies one’s gay awakening.

In many ways, Charles Herman-Wurm bears the familiar tropes of many LGBTQ films from its period. Jessica is like many women of her era, going through the motions of life without any consideration for her own happiness, living life according to someone else’s vague theory of how it should be lived. A good chunk of the 97-minute runtime is dedicated to Jessica’s reluctance to leave the closet, a sentiment that’s still sadly relatable to many more than two decades down the road, at great expense to the film’s more interesting plotlines.

 Westfeldt and Juergensen, who co-wrote the screenplay, possess impeccable chemistry. As Helen, Juergensen brings that vital magnetic Type-A Gen X lesbian energy, the kind of force of will destined to stay with someone regardless of what happens to a relationship. Many of us have had a Helen in our lives who saw us before we could completely see ourselves, who stood up and spoke out against the false comforts of the closet. 

Kissing Jessica Stein rises above many of its rom-com trappings to display a remarkable level of maturity. The nature of Jessica’s sexuality sits at the heart of the narrative, but the film never falls into the trap of making bisexual people pick sides. Feldshuh helps anchor the emotional core of the film with a powerful supporting performance.

In many ways, the film conjures natural comparisons to Sex and the City and other pieces from the early aughts centered around the existential crises facing young adults among New York’s upper class. Kissing Jessica Stein doesn’t exactly bring anything new to the table, but there’s a certain charm to be found in this endearing queer romcom. LGBTQ people are often expected to have all the answers. Perhaps Kissing Jessica Stein’s greatest triumph is that it doesn’t pretend to.