Although they didn't realize it immediately, Heather Juergensen met Jennifer Westfeldt at a New York theater retreat late in the '90s.
Two unknown actors would co-create and then produce "Kissing Jessica Stein" in 2002. They had been discussing similar ideas, namely how awful it was to date in your 20s, particularly if you were dating men.
Juergensen stated, "It was a nice little workshop run in New York City by an theater, who took all their actors and directors, writers -- everybody who wanted to travel -- up to Catskills every year." It was encouraged to do something that you had never done before. If you only acted, then you were instructed to write or direct and vice-versa.
Juergensen had created a sketch and asked Westfeldt for it to be performed. Westfeldt declined to act in the sketch because she had already signed up for too many retreat projects. As Juergensen describes it, "everyone wanted Jennifer."
They formed a friendship and soon discovered their common interest in modern love. Westfeldt recalls that they both created a sketch of a "nightmare date" and then clocked each others. "One of us suggested that we rent a theater to put up a night full of vignettes. Then, it was cut to one year later."
After a short stint in Los Angeles Westfeldt realized she missed New York theater and theatre so she returned to New York. Heather called her upon arrival and asked, "Remember me from the Summer?" We talked about the theater. Let's do it."
Juergensen had just returned to her home with her parents after she was unable pay the rent increase at her co-op. As she was sitting in her childhood bed, feeling disorganized and considering the hardships of being a creative, Westfeldt called.
"We put together a group and rented a space in the basement at a church. We started writing," Westfeldt explained. This was the beginning of the play that would eventually become "Kissing Jessica Stein." The two women were considering trying it together.
Even though the play "Lipshtick" was only viewed for one weekend, it attracted attention from a few studios who saw the potential to make it into a movie.
Juergensen & Westfeldt have a natural chemistry and a tendency to end each other's sentences. Westfeldt recalled that moment as the beginning of the long process of making the film.
Juergensen interrupted, punctuating the thought.
This idea became "Kissing Jessica Stein", a film about two women trying to find a relationship after feeling exhausted by New York's male dating scene. Westfeldt plays the title character. She is a neurotic copyeditor who is held back by her perfectionist standards. Juergensen plays Helen Juergensen. She places a personal advertisement for Helen, a free-spirited gallerist. They fall in love and discover the joys of sapphic sex. Jessica's real challenge is to decide if her love for Helen extends beyond platonic.
"We have had some amazing, long-lasting friendships with our girls. It felt like a small leap. It was that moment that it all began: we explored those amazing bonds with other women, which felt so real, deep and intimate. Westfeldt added, "What if?"
Juergensen & Westfeldt had to search around for the right studio to bring their idea to life and let them play the lead roles. Gramercy Pictures eventually optioned their script with the understanding that they would portray Jessica and Helen.
It was all a very dreamy moment. "We wrote this little play and it was my first sitcom. It still felt like an immense leap and an amazing opportunity," Westfeldt stated.
After two years of work on the script together with the studio and no sign of an end, reality finally set in. They feared that the film would languish in production limbo for many more years. Juergensen & Westfeldt purchased the rights back to the film and started the journey of making it independent. This required funding and a team who was completely committed to their vision.
They sold shares at $2,500 each to anyone who could purchase one, or half, of the shares. They found an angel investor who funded a significant portion of the modest film's budget. They had already signed on several friends to major roles behind the scenes, including Eden Wurmfeld as executive producer and Lawrence Sher as cinematographer.
"We started to collect people from our extended circle. Westfeldt stated that you were either in 500 percent of the group or not at all. That was how it came together.
It's difficult to make a movie on your own. The good news is that only the people who invite you to your party will be invited. Juergensen agreed that we were able to gather a group who were, Jen said, "all in" and had the material. They were also very committed to the vision.
They eventually chose Charles Herman-Wurmfeld as their director, thanks to this inner-circle strategy.
Juergensen & Westfeldt approached and turned down more experienced directors. Juergensen and Westfeldt chose the enthusiastic, green director who had just moved to LA to pursue a career as a filmmaker after having worked in San Francisco's theater. Herman-Wurmfeld was in his sibling's living room, sleeping on her couch and working at a cafe while he toured the city by bicycle.
Herman-Wurmfeld, unlike the other major actors in the film, was familiar with queer storytelling and was interested in directing a sapphic love story. He was particularly drawn to the conflict that occurs when Jessica can't match Helen's passion for intimacy and being a card-carrying queer.
"I felt very connected to their story, as someone who came out with their best friend who was straight and had seen their gayness through someone else's eyes. It was very vibrant and true to me," Herman Wurtzfeld stated.
He didn't have much film experience, so it was a difficult task to become a director. But his patience paid off. "I chased it. Herman-Wurmfeld stated, "I would not stop making myself available for help in any way possible. And I truly meant that."
"I was trying to be a director but I was willing to take on the project wherever they would have me. They realized that many people rejected their offers and ended up saying that they needed a director who loved the story. It doesn't matter how well-known they are, as we already have our money together. He explained that it was becoming less important for creators to hire a big name.
After Juergensen & Westfeldt had made their decision about the director, the cast was completed with some more familiar faces like Scott Cohen (who plays Jessica's ex-boyfriend and current boss Josh) and Tovah Feldshuh (who plays Jessica’s overbearing Jewish mom).
Feldshuh was in the forefront of the plan, but Cohen, well-known for his role as the "10th Kingdom" miniseries, ended up being an unexpected asset.
"He wasn’t our first choice. You think you want something, and then the world (shows you) what you can get. This is a common thing in indie filmmaking. Then, you realize that this is what I needed all along," Herman-Wurmfeld stated about the actor who was eventually cast as Jessica’s infuriating and charming admirer. "Scott was able to play that role and became a foil for Jessica's affection for the -- a little bit looney - character.
Cohen admitted that he didn’t see the impact of "Kissing Jessica Stein", but he believed in the creators and cast members. "Indie films feel like independent films because there’s usually somebody so inexperienced that it’s hard to know what they’re doing. This did not feel like this.
There were still signs that they were indeed working on an independent film. Cohen mentioned that he sat on an apple box in the street between scenes to avoid waiting for a trailer. He mainly remembers that his character and the film felt real to him, with all its flaws and missed opportunities.
It's amazing that there is an arc to his personality. Cohen stated that Cohen can show you where he begins, what he becomes, and what he is missing.
He's not seeing Jessica. He realizes this, and she has the courage to speak out about her relationship.
There are a few scenes at the end of "Kissing Jessica Stein" which stand out among the lighthearted, often slapstick film. Josh is shown in the scene where he reflects on his feelings and the relationships he has been missing. The other is Jessica's heart-to-heart with Judy, her mother.
The emotional scene featuring Feldshuh and Westfeldt shows the mother offering an olive branch to her daughter. She can't seem to accept her relationship despite falling in love. Judy senses Jessica is hesitant to express her emotions and breaks the silence by bringing up Helen. She utters a simple, but meaningful compliment about Helen's being a nice girl.
"Before she said, 'I think that she's very nice girl', she takes this moment and swallows everything she had thought. It becomes a moment when you can see the character having this human experience, of putting the past into the present and stepping into another place," Herman-Wurmfeld stated, repeating the scene Feldshuh had just described to the others.
Although the moment's turmoil is dated by modern standards, in which queer identity and love are openly celebrated onscreen, it resonated with many LGBTQ viewers. This was an era when the closet was still a very normal place to be.
"Strangers approach me on the airplane, or in line to get something, and they say, That scene really changed our lives' or 'That is the scene that I showed my parents'," Westfeldt stated, referring to the experiences she and Jeurgensen still have. It's been a source of inspiration for people who don't come from a supportive or liberal family.
"That's probably my proudest moment as an artist. It's the best thing I have ever done for anyone being able come out."
Although that scene is fondly remembered by LGBTQ viewers, "Kissing Jessica Stein", which was released in 1995, was divisive. Although it isn't the only example of the era, many queer viewers were offended by the film's premise. It featured two women exploring a same-sex relationship in casual conversation. However, many people were grateful for the representation in a time when mainstream romances were exclusively heterosexual.
These criticisms were not unheard by Juergensen or Westfeldt, who even altered the ending of the film, which had Jessica visiting Josh's home to check on his romantic confession. They redid the last scenes, which were seen as both symptomatic and sympathetic to the film’s straight roots. Jessica meets Josh under more ambiguous circumstances but ends up having a friendly lunch at Helen's. Helen has now found her way into a healthier, more sexually-positive relationship.
Juergensen reflected on the past and said that "our earlier ending felt a bit quick and truncated" and that Jessica had not evolved in the way people expected. "We felt that we needed both women in the relationship to be more authentically who they are."
Except for the ending, Westfeldt & Juergensen stated that they would not change anything.
"There was a sense of utter utterance about the shoot, and everyone was being there together. It was something that you couldn't capture if you had twice as much money or everything was labored," Westfeldt stated. It was us against all the odds, so there was just a sense of humor and spontaneity.
"The energy in the film is what people respond to, I think. It was all the things you couldn't buy. Juergensen said that they are just that; they have the urgency."
Their director is also in agreement. He hopes that the film, which he calls "a love letter for queer people" and being rereleased within the context of LGBTQ Pride Month in June will finally be appreciated by queer audiences.
Herman-Wurmfeld stated, "This is why i became a filmmaker because I believe that the stories that we tell ourselves are liberating." Talk to children and you'll find that they freely express their gender fluidity. Stories like these have helped to ease that, I hope. The story is not just for us, but it has had a significant impact on many others."
It was a turning point in my artistic career. It's 20 years later and we still talk about it. That's a dream come to life -- that there's still relevance for something we did so many years ago.
Today.com first published this story.