The secrets behind Kissing Jessica Stein, a rare LGBTQ romcom

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Jennifer Westfeldt and Heather Juergensen met at a theater workshop in upstate New York, each working on material about NYC’s dating scene. And from that kernel came Kissing Jessica Stein, about Jessica (Westfeldt), who searches for the perfect guy and finds Helen (Juergensen), who might just be the perfect woman, an option that she’s never considered. The Kissing Jessica Stein cast came together to unearth stories from the little gem of a film that grossed only $7 million but has become a major touchstone for the LGBTQ community.

Kissing Jessica Stein was a small production, and often shot in friends’ and families’ homes. When filming at Westfeldt’s parents’ house in Connecticut, Scott Cohen (who played Jessica’s prickly boss Josh) was mistakenly arrested while getting coffee at a nearby deli. “I hear this siren behind me. This cop gets out of his car, and he puts my hands behind my back and handcuffs me,” he says. “I had no idea what was going on, and he tells me that there’s this guy who’s been robbing delis in the area.” Cohen called producer Eden Wurmfeld about his arrest, but before Wurm­feld arrived at the jail, the police had released Cohen. “Finally this detective comes and he pulls out this picture, and he was like, ‘This is not you, we’re really sorry.’”

One of the best scenes in Kissing Jessica Stein is the conversation between Jessica and her mother, Judy (Tovah Feldshuh), on their front porch, when Judy acknowledges Jessica’s relationship with Helen. While the chemistry came from the writing, it was enhanced by the time that Westfeldt worked as Feldshuh’s assistant. During that gig, Feldshuh remembers how much comfort Westfeldt offered her as her father was dying. “There was a knock on my father’s hospital door. It was Jennifer Westfeldt, and she said, ‘I didn’t want you to be alone,’” Feldshuh recalls. After that, the actress knew she’d do anything for Westfeldt.

When looking for a director, initially Juergensen and Westfeldt wanted someone with more experience, since they themselves were so green in the movie-making process. Westfeldt had called up Eden Wurmfeld, a friend of hers, who was a pretty experienced indie film producer and, as Westfeldt describes, the “adult” of the group. Wurmfeld’s brother, Charles Herman-Wurmfeld, at the time, had only one small experimental film under his directing belt and fought to helm the film. There was a thin connection to Doug Liman, director of Swingers, who would “supervise” Charles to direct, which didn’t happen because Liman went to direct The Bourne Identity. And while Charles may not have had the experience they wanted at first as Cohen recalls, he “really understood what they [Westfeldt and Juergensen] wanted.”

There’s a lot of random celeb spotting when watching Kissing Jessica Stein today — stars like Idina Menzel and Michael Ealy show up. And comedian/actor/director Michael Showalter appears as one of Helen’s many lovers in an early scene. It’s something that wouldn’t be terribly memorable if Showalter didn’t talk about hanging a bookmark off his genitals — making the library system dirty. According to Juergensen, being able to do his own thing was the only way he’d do it. “He said, ‘I just basically want to do some ad libbing on set with you guys.’”

While Scott Cohen ended up playing the role of Josh, as recommended by Camryn Manheim, Jon Hamm originally read for the part with Juergensen and Westfeldt. If you are a Kissing Jessica Stein superfan, you’ll know he has a small role as a guy Jessica’s friends try to set her up with in the beginning of the film. Juergensen said that when it came time to cast the role, they, of course, wanted to cast Hamm as Josh. But the investors wanted a name or a Noah Wyle type, and Cohen had a much more solid body of work at the time, so they ended up casting Cohen instead and loved the work he did as Josh.

While some audiences still were disappointed with the Kissing Jessica Stein ending (Westfeldt jokes about always having divisive endings in her films) the original really pissed people off. Juergensen says the ending they originally shot had Jessica go to Josh’s house with clear intentions of seeing him, instead of them running into one another. “That was the other thing that audiences, especially gay audiences, were like, are you kidding me? So Helen is just this ridiculous footnote in her life and all she ever wanted was Josh.” So they all regrouped and, as Westfeldt mentions, having a gay director was imperative in making sure they were being respectful and responsible for the journeys of these characters. And that’s why they ended up having Jessica bump into Josh, as opposed to having her more actively pursue him, so it didn’t feel like it nullified her relationship with Helen.

The film earned critical acclaim at release but also garnered criticism for its ending (Jessica and Helen — spoiler alert! — don’t end up together). Yet it still resonates with the LGBTQ community. Jackie Hoffman (Feud), who played Jessica’s pregnant BFF, remains proud of the film. “Lesbians, first of all, love it. One time it was a cop who says, ‘Weren’t you in the movie Kissing Jessica Stein?’ I think it’s been more than one cop, oddly enough. When people see me, to this day, they still talk about it.”