Fake pregnancies! Taxicab confessions! A bit player named Jon Hamm! What it was like shooting the little indie that could, in one of the romantic cities in the world.

In 2002, Will and Grace was only halfway through its 8 seasons; The L Word was still two years away; and we were three years from the premiere of Brokeback Mountain, the tragic story about repressed love between two cowboys that was once held as the gold standard for what LGBTQ+ audiences could expect when it came to representation in mainstream Hollywood.

LGBTQ+ characters have come a long way in the last two decades (just take a look at our Pride month cover stars Joel Kim Booster and Billy Eichner for starters), but there have always been outliers — films that gave audiences a chance to see a glimmer of themselves on screen, even if the film itself is imperfect.

One such movie was 2002 rom-com Kissing Jessica Stein, in which the uptight Jessica Stein (Jennifer Westfeldt) finds herself answering an ad for a "woman seeking woman" in the paper — and falling in love with Helen (Heather Juergensen). But as the two women explore their sexuality, can Jessica let go of her hang-ups enough to love Helen the way she deserves? And even if she can, is that enough?

Kissing Jessica Stein
Credit: Everett Collection

Beginning as a stage play co-written by Westfeldt and Juergensen, Kissing Jessica Stein is a queer rom-com that delved into questions of identity, self-acceptance, and sex in ways that were rarely seen in movies at the time. Some decried the film's conclusion, in which — 20-year spoiler alert! — the two heroines break up. But it still marked a milestone for lesbian and queer representation.

In honor of the groundbreaking movie's 20th anniversary, we gathered the team behind the film, including co-writers and stars Westfeldt and Juergensen, director Charles Herman-Wurmfeld, producer Eden Wurmfeld, cinematographer Lawrence Sher, and cast members Tovah Feldshuh, Jackie Hoffman, and Scott Cohen to reminisce about what it was like making the cult classic.

As working actors, Heather Juergensen and Jennifer Westfeldt met at a theater retreat and had the spark of the idea that would eventually become Kissing Jessica Stein.

JENNIFER WESTFELDT (CO-WRITER/JESSICA): Heather and I met at this really fun theater retreat in the Catskills for writers, directors, and actors.  Everybody was asked to do something they didn't know how to do. If you were a director you had to act, and if you were an actor, you had to write something. We both ended up writing a sketch that was about a horrible date, and we clocked each other. We stayed in touch after that retreat.

HEATHER JUERGENSEN (CO-WRITER/HELEN): We started doing staged readings of this material for our friends and acting network. Jen and I regrouped and said, "What if all the bad dates is act one? These two women are going crazy in the dating scene, it's not working. And then act two is after they get together?" Right after we finished, Jen's agents were calling saying, "HBO's calling, and all these people are interested in developing this." So, we were suddenly thrust into screenwriter-ville and the development world.

WESTFELDT: We decided to make it indie after we had gone the studio route and felt like it would never get made. We got bounced around so much that we said, "Let's just make it indie. Let's get a camera. Let's get some cash and just do any version of this we can." And that's when we reached out to Eden and we started doing readings, and raising money, and found Charlie, and that's how it all began.

JUERGENSEN: Remember, the last meeting with our executive from the studio system when we said this, he paused and he said, "Do you mean you want to make it with orthodontists?" And we were like, "Yep, we're going to go to orthodontists and ask for some checks." And that's where [producer] Eden Wurmfeld came in because Eden had a background in raising money privately. People watching true indies don't realize how much goes into the hustle to raise that money. It was really a grueling period.

EDEN WURMFELD (Producer): There's an expression in Russian that translates to "make a candy out of s--t," and I always think of that when I think of this movie because I feel like we really did it. We made something beautiful and enduring.

Kissing Jessica Stein
Credit: Searchlight Pictures

Once they decided to go indie, they also needed to secure a cast, a director, and a production team. Director Charles Herman-Wurmfeld was still very green, but he was passionate about the script. They originally wanted Westfeldt's then-boyfriend Jon Hamm to play Jessica's boss, Josh Meyers, but Hamm was committed to another project.

CHARLES HERMAN-WURMFELD (Director): I remember reading this script and thinking, "They wrote something so beautiful," and that it was going to be the perfect expression of this queer love story or gender fluid story where our sexualities are open to our interpretations as we move. I really didn't have a lot of credits to my name at that time, and I was chasing something that was a very far away dream. I was working at a café on Melrose, where Jen and Heather came to drink coffee and talk about the script. I remember chatting them up every time I could and telling them how beautiful their story was, and how if they ever needed me for anything, I was available. I was ready to come and do craft services if necessary.

WURMFELD: As his sister, I can say he was not at the top of the list.

LAWRENCE SHER (Cinematographer): Kissing Jessica Stein has such an important place in my history. A friend of mine connected me to Jen, and then got me a chance to meet with Charlie. Jen met me at an airport restaurant. It was a real watershed movie for me because I was 30 years old, and I had decided that year that I was never going to take any more work as a camera assistant or anything else. That I was just going to try to make myself be a cinematographer. Here it was September, and I hadn't earned a single dollar that year. I was freaking out a bit. When the call came, it honestly was the most important film in my career to finally give me opportunities that I didn't have before.

KISSING JESSICA STEIN 2001Jon Hamm (screen grab)CR: 20th Century Fox
Credit: 20th Century Fox

WESTFELDT: Jon had [played Josh] in the play, but he wasn't available. He was on this show called Providence at the time. So, we started the audition process.

JUERGENSEN: Scott at that time was "offer only "for a project like this. And we were like, "Oh gosh, it's such an important role. Please, please, please read for us. We just want to hear it." And Scott, you very graciously read for us.

SCOTT COHEN (Josh Meyers): Yeah, I remember that. I remember doing the dinner scene and seeing Jon in that scene and saying to Jennifer, "Hey, why isn't this guy playing this part? I don't really get it." But that was that. I had no idea who he was.

TOVAH FELDSHUH (Judy Stein): Jennifer Westfeldt, at one time in her life, was my assistant. On May 11th, 1996, my father Sidney died. And he was the king of my life. I was alone with his body in White Plains hospital. There was a knock on the door. And it was my assistant who had worked for me for only 90 days. And Jennifer said, "I didn't want you to be alone with your dad." And I said to her, "If there's anything I can do for you, if there's any kindness, any favor I can do for you, the answer is yes, it's already, yes." Later, Jennifer asked me to come see her play. It was called Lipshtick. And eventually that "favor," would be, "Would you play my mother in what was Lipshtick?" I said, "I give my word. I will play your mother, but you need to give me more material." And they did. I actually thought maybe Jennifer and Heather understood me so well that they custom made parts of the character because it just fit like a glove. We may have shot on a very low budget and I may have worn most of my own clothes, but it's still a highlight of my career.

Kissing Jessica Stein
Credit: Everett Collection

With the cast and crew assembled, they set about filming on location in Connecticut and New York. We see Jessica and Helen as they go to work (Jessica as a reporter, Helen at an art gallery), go on terrible dates, and hang out with their friends, including Jessica's co-worker and best friend Joan (Jackie Hoffman). When Helen and Jessica finally meet, they have a lengthy date that traverses New York City, including hopping in the back of a cab where they discuss lipstick application.

WESTFELDT: We always said that the city was another character in the film.

SHER: It was very important for me to make it feel like what New York is, which is one of the most romantic places in the world. And to shoot in real locations and all of those things.

WESTFELDT: We didn't shut down a street. We were in the street, and it was a green light and we'd go, "Go. Roll the film." I'm trying to hail a cab, and we're almost getting hit by cars.

HERMAN-WURMFELD: We should tell the story about the taxicab.

JUERGENSEN: This is where Helen and Jessica are discussing the lipstick.

HERMAN-WURMFELD: We just hailed a cab and jumped in.

SHER: Charlie was stuffed next to the driver. The camera was in the middle, right between the seats. Basically, the sound person was in the trunk.

WESTFELDT: The moment in time that was in New York, you'd still have cab drivers back then who were like, "I don't know, this is New York. Just go with it."

JACKIE HOFFMAN (Joan): In another scene, we were shooting outside at night and I had that fake pregnancy pillow on. These guys from the street watching just kept yelling out, "Hey, pregnant lady. Hey. Hey, pregnant lady." So, I kept running with my stomach and slamming the fake pregnancy into a wall just to freak everybody out. And Charlie said to me, "Okay, don't do that."

They made the film in New York a year before 9/11, but by the time they screened at the Toronto International Film Festival in fall 2001, the city had undergone a massive change in its skyline and was recovering from the tragedy.

SHER: There was a screening right before 9/11 and then there was another one after in Toronto. And the one after was just fundamentally too hard to watch.

JUERGENSEN: People were audibly loudly gasping in the theater.

HERMAN-WURMFELD: It wasn't like they were just there. We were utilizing the towers to represent these two iconic characters. And so, there were gasps in the audience every time we went there. It was a lot.

WESTFELDT: There were eight shots of the towers. It was an incredibly difficult decision [to remove them]. All of us were on email threads about it. There were pros and cons to leaving them in. Ultimately, we all decided that it was a comedy and it was coming out in March and it was just too soon to trigger audiences when we really wanted to uplift audiences. Maybe if it had been later, we would've made a different decision, but we did the best we could in that moment. I know we were all tortured about it.

On their date, the women end up walking together, passing a group of Hare Krishnas that sparks Jessica to meditate on trying new things and knowing certain things are just not for her.

SHER: We were trying to find a location to shoot a little walk and talk, and we were riding a bicycle. I feel like I was on the handlebars, but I was probably on the back, as Charlie and I were trying to find a location. We were hungry and went to get some pizza, and then we look out and we're like —

HERMAN-WURMFELD: This is the place.

JUERGENSEN: The scene where Jen and I are walking past the Hare Krishnas and Jessica is like, "They're ridiculous" — we had some interlopers. Some guy who was just like, "Haha, I'm in a movie now." And we're like, "We're actually shooting. Could you please not do that? We don't have a minute to spare." Because our days were so tight.

WESTFELDT: In that same sequence, I was totally new to camera. I was only a musical theater and theater person. We were getting changed and in hair and makeup, so we had wet hair. Charlie ran in and was like, "The light's beautiful. Larry wants to shoot a wide shot of you guys arguing as you cross the street." And we were like, "What? Here?" We looked terrible. We're like, "We have curlers in, and we were not dressed." And Charlie was like, "This is important to Larry." We were like, "We're going to look ridiculous, but all right." And of course, it ended up this fantastic wide shot of us fighting as we're arguing with our hands as we crossed the street in the crosswalk. You couldn't tell that our hair was wet. It just looked like a beautiful shot.

SHER: I probably was a little bit less tactful. I was like, "Get them out." But after finding that street and having great pizza, we had to map out that whole walk and talk, and cross the street and you kiss. We had limited lighting. It was like that crossing the street shot, which to me, anytime you're in live New York that's quintessential. It's what New York gives you for free, which is amazing production design just by being out in the real world.

Kissing Jessica Stein
Credit: Everett Collection

Their conversation about trying new things prompts Helen to surprise Jessica by kissing her, encouraging her to broaden her horizons.

WESTFELDT: Everything went through a zillion iterations because we were writing and rewriting for years while we were hoping to make this. Heather, do you remember how we came up with that ending?

JUERGENSEN: I remember that the whole first date sequence was really tricky from a story standpoint, because we had drawn Jessica Stein as this woman who was very uptight and very, very, not apt to just kiss another woman on a first date. Why is she even on the date? It was outlandish for that character. So, we had to really craft the date both on the page and in the shooting as this amazing journey that the two women are going on, with all these little moments. At the end, with that kiss, there had been so much connection that even Jessica couldn't deny she's vibing with this girl. It was tricky though. I think it was 13 pages. That's too long for one scene, but it was this ebb and flow of little scene-lets connected. We felt that this is really the crux of the movie right here and we better get it right.

WESTFELDT: Heather remains the only girl I've ever kissed.

Kissing Jessica Stein CR: Courtesy of Eden Wurmfeld
Credit: Courtesy of Eden Wurmfeld

Helen and Jessica begin seeing each other, with Jessica becoming increasingly more comfortable with kissing another woman, as a montage shows the progression of their physical intimacy.

JUERGENSEN: At that point, Jennifer and I were like an old, married couple. We had been developing this script for so long. We had done so many workshops. We had done that particular scene of the montage of like, "Should I touch you? And is it tongue?" And all that type of stuff. That was really all the way back to the play; it was one scene in the play. At that point, our chemistry was so steeped and we were so together that at least for me, it felt very easy. In a weird way, we had to act like it was more uncomfortable than it was.

WESTFELDT: There was also a shorthand of just being able to try and capture certain insecurities that certain women have. In the play, one of the bad dates for my character, it's going well, and then I'm like, "Oh, don't touch my stomach." And it would always get a laugh. In the movie, we don't have that line, but there is that thing where Helen almost touches Jessica. It's just funny how it evolved from the sketchier version to the subtler version.

COHEN: I remember the long conversations about the theatrical aspect of this beautiful script and how we were going to offer this film as a movie. And understanding that we were going to sweep the camera through and let time pass, and let there be motion amidst this very static, scenic moment sitting on the couch over time.

Kissing Jessica Stein
Credit: Moviestore/Shutterstock

As things develop, Jessica struggles to keep her relationship with Helen a secret. Her best friend at work, Joan, is one of the first to find out when Jessica confesses the truth of their romance to her, and her shocked reaction is, "Lesbians?!"

HOFFMAN: I haven't had a part like that before that or since. In a career of always being told to be small, small, small, small, small, and Charlie, let me go huge, crazy, but still keep it real. I remember running around in this Upper West Side apartment shrieking, and it was just so cool. It felt like the joy you feel of being on the stage. It felt that immediate and that honest, and not like this tired, "Take 89," that you get with film fatigue.

HERMAN-WURMFELD: Oh, I remember that day, Jackie. It was a beautiful day. I remember our conversations behind the scenes. And that agreement we made to let it be free. You really did.

HOFFMAN: To this day, lesbians stop me on the street and say, "Lesbians?" It's become this iconic moment.

WESTFELDT: That was another borrowed apartment. My dear friend, Haley, her old studio apartment. Almost every location was somebody's that we knew.

JUERGENSEN: Wasn't that the building, Eden, where some other resident was grumbling and you said, "We're making movies, it's the magic of movies." And they were like, "You can take your movie magic and shove it up your ass."

WURMFELD: It was absolutely that building. It was the Upper West Side. I just remember the film office kept not wanting to give us permits because they said that every location we had chosen was what they considered the "Nagasaki of New York filming." They were like, "You can't shoot here anymore." So, we had some very pissed off neighbors.

KISSING JESSICA STEIN, Tovah Feldshuh, Jennifer Westfeldt, 2001, TM & Copyright (c) 20th Century Fox
Credit: Everett Collection

After Jessica and Helen have a fight over keeping the relationship secret, Jessica's mother realizes what's happening and they have a late-night heart to heart on the porch where she gently acknowledges her daughter's relationship and offers her love and support.

FELDSHUH: I think it was two in the morning.

HERMAN-WURMFELD: It was. It was the last of the day.

FELDSHUH: And we were at Jennifer's mom's house?

WESTFELDT: My mom's friend.

FELDSHUH: I remember resting and being awakened to do the scene. We shot it in two takes because Charlie said to me, "We don't have enough film." Sometimes it's hard to watch yourself in films. This was an incident in my career where I thought I was better than I remembered. I loved the constriction of it. I loved Charlie's gentleness with it. I love the demands that we had to shoot it quickly. That scene was a gift. That scene has gotten me acknowledgement and has been a hallmark in my work.

SHER: With time constraints and all these practical things that come into filmmaking, you sometimes can lose sight of the present. But at that moment, even though it was so late and it was the end of a long day, everyone was genuinely tearing up behind the lens and going, "Yeah, this is amazing. This is such a beautiful moment." When you have those moments where you're completely present, the whole day is washed away and you're just seeing through the lens. I remember thinking, "If the whole movie's like this, then we got something."

HERMAN-WURMFELD: I remember that too. Just sitting there going, "Something awesome just happened." Tovah, you became like the moon herself, just beaming love.

SHER: I remember thinking, "I'm going to commit to hold that space and not use multiple angles and just sit there with them."

KISSING JESSICA STEIN, Scott Cohen, Jennifer Westfeldt, 2001, TM & Copyright (c) 20th Century Fox Fi
Credit: Everett Collection

Jessica and Helen resolve their fight, and Helen comes with Jessica to a family wedding. Still not quite aware of what's happening, Josh confesses his feelings to Jessica on a moonlit rooftop, a perfect rom-com moment — but she chooses Helen, who whisks Jessica back to the party.

WESTFELDT: We were in the armory in Central Park and they had never had a shoot there before. Jon's friend worked for the Parks Department and pulled some strings. All of our friends and family were the wedding guests. It was not unlike the shot with the wet hair, where we were just waiting for magic hour. Scott and I had a lot of chemistry that we built through the shoot. It was so easy to play off each other. I did feel really torn in the moment — the way Jessica does — where this is a sliding doors, could have, would have, should have, but I'm in this other thing too, and I got to give it a go. There was something really nice about her feeling that if this had come just six months ago or a year ago, it would've been so welcome. That's just so much the way life is; that the timing is just slightly off.

COHEN: I remember feeling so fragile and so vulnerable in a moment that you're giving so much and then not getting what you think you want. And then life changes. I remember the night sky and the city behind us. I loved it.

WESTFELDT: There was so much chemistry between Heather and Scott as well. It felt like a very powerful triangle.

JUERGENSEN: I do remember making a little meal out of that last look I shoot him, of like, "Oh, well I got the girl. Later, potato."

COHEN: I think we need to do a Kissing Jessica Stein 2, just saying.

Kissing Jessica Stein
Credit: Searchlight Pictures

Despite moving in together, the physical intimacy between Jessica and Helen dwindles, pushing Helen to break up with Jessica. The two don't end up together, but they remain friends. After test screenings, they reshot one of the final scenes in a bookstore where Jessica runs into Josh to make their meeting more ambiguous, and honor her journey of self-discovery.

WESTFELDT: This whole team was just like, "How do we land the plane and show the passing of time and that they're going different directions?" But the main thing we wanted to land was their friendship. Whether or not Jessica was going to get together with Josh, who knows? We just wanted to show the changes and end on the two women as thick as thieves.

JUERGENSEN: We had a totally different ending, and it was early audiences that said, "It doesn't feel right the way they break up. It doesn't feel right the way Jessica ends." And that was the real catalyst for, as a team, discussing all those things.

HERMAN-WURMFELD: It was subtle changes.

JUERGENSEN: Jessica was more nervous when she ran into Scott's character. A little more like still the old Jess. Jennifer referred to it as "the curly-haired scene." We said, "Clearly her experience with Helen has allowed her to unfold herself and to let loose a little and to be this new version of herself, where she's more able to meet Josh holding her own."

HERMAN-WURMFELD: This is why we love this character, because it's a liberation story. And that is such a beautiful offering to the world.

WESTFELDT: My classmate from college [plays the other girl] in that bookstore scene. And I remember some people were like, "Oh, I thought she really liked the girl in the bookstore." It was fun that we were able to find more of that ambiguity, but [it was] the larger point that they had both come a long way, that they both were whole and would be happy, but only as dear friends.

JUERGENSEN: The revised version of the bookstore scene honored more what had transpired between Jessica and Helen.

Kissing Jessica Stein CR: Courtesy of Eden Wurmfeld
Credit: Courtesy of Eden Wurmfeld

WESTFELDT: We always knew that we wanted to explore the notion of one of the women really identifying her biological truth and the other being more fluid and on the continuum and it not being as clear for her. At the time, we had a lot of blowback about it. But it was important for us to show two different stories here. One where Helen is like, "This is who I am. This is my identity. It's not a choice for me. It's not fluidity. It's who I am." And the scene where Jessica's saying like, "But we're best friends. This is the best relationship I've ever had." Essentially like, "Isn't that enough? I love you so much." And it wasn't enough for Helen because she really needed that sexual chemistry and that passion. The difference in their experience of it was an important distinction to show.

JUERGENSEN: To me, the reality that these two women had very different experiences of this relationship. That happens. The essence of the story was that one woman was exploring because she wanted to with this person, but ultimately, she wasn't gay. So, she couldn't be with this person for the long haul. My character, on the other hand, was gay. She had been with men because that's societally what is the starting point. But when she explored it, for her it was a revelation. For my character it was, "Oh, this is who I am." So I thought that complexity and allowing each woman to have such a unique experience, that was the more nuanced storytelling.

WESTFELDT: I felt like Jessica would've stayed in it forever though. Because she loved her and that was enough for her. So, it was more that because Helen had been broken open in this way, that she was like, "Nope, not enough for me."

JUERGENSEN: That said, we certainly had some women at early screenings who expressed profound disappointment because gay women and gay people at that time had fewer stories with a happy ending.

HERMAN-WURNFELD: Many queer people come out with their more straight best friends in sexual relationships. Now, after 20 years have passed, you're seeing that fluidity in action. It's so beautiful that we created a flagship narrative from a time period from which so many stories have come now. There is no longer a dearth of queer stories that people are going, "We need this story to tell every bit of our experiences as queer people." I think the reception now for the movie will be even warmer from its queer audiences because that pressure is off. We can just enjoy the fun of watching Jessica squirm through her experience of discovering who she is and what she wants.

Kissing Jessica Stein is streaming now on Hulu.

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