Heather Juergensen and Jennifer Westfeldt met while attending Ensemble Studio Theatre's Summer Conference in New York's Catskill Mountains in July, 1996. The conference is an annual event where actors, writers and directors come together in a retreat setting to develop new material and 'cross-pollinate' -- i.e., directors are encouraged to act, actors encouraged to write, and so on. Heather and Jennifer, though actors first and foremost, both did some experimental writing that week and noticed they were writing on a similar theme- namely, "dating hell" and the comedically charged communication gap between men and women. They thought it would be fun to band together and create a night of theatre with this theme as the unifying thread.

The next summer they began work on the piece. Of all the scenes they began crafting about the hazards of dating - with the actresses planning to play many different women throughout the night -- one scene in particular sparked their imaginations… "Two Laura Ashley-clad girly-girls, fed up with men, meet at a day spa to negotiate how to become lesbians." While broad in its execution, the actresses gradually realized that this one sketch was more comedic, more compelling and, at a deeper level, more interesting than anything else they were working on. With the assistance of their able director, Robert Davenport, they realized that the many different women they were depicting in the many different bad dates were actually the same two women - Jessica and Helen - navigating through their separate journeys only to finally wind up on that momentous date with each other. Through a truly organic, collaborative creative process, they realized they had written a play-- act one focusing on 'dating hell', and act two on the relationship between the two women.

Over a six-week period, with an ensemble of actors in place, Juergensen and Westfeldt worked extensively on the script. They held regular roundtables with their colleagues from the New York theater community for feedback, and also spent many hours talking to women -- gay and straight -- who had lived some version of the story they were creating. The play, called Lipschtick (the story of two women seeking the perfect shade) ran for only six nights -- Oct. 24 - Oct. 29, 1997 -- at the ArcLight Theater in New York's upper west side.

Though the run was small, audience reaction was not. People came and then came back again with friends… every night was a sold-out show. Somehow a cross-country buzz was generated. As Heather tells the story, "Only a week later, I was talking to an agent at CAA who said she had just been talking about us at her staff meeting that morning! Incredibly, our tiny little play had hit the radar in Hollywood."

This led to immediate interest in adapting the material to film - both at the studio level and also the smaller, more independent level. The women were excited to make this happen, as the play had only begun to scratch the surface of the complexity of their premise. So in December 1997, they holed up for a few weeks and - borrowing Heather's boyfriend's screenwriting software and Jen's parents' country house - they gave themselves a crash course in screenwriting. They were eager to open up the world they had created in the play by expanding locations, invoking background characters the play had not had room for, and honing the theme. Admittedly, they went a bit overboard in their newly adopted medium, with their first draft clocking in at 162 pages. "We liked to call it 'Kenneth Branaugh's Lipschtick'," Jennifer jokes.

By April 1998 the girls had honed their opus down to a more appropriate length, and the property was optioned by Interscope Communications (then a division of Polygram Filmed Entertainment, with a pipeline through Gramercy), with the women attached to star. Other studios had expressed interest in the script as a property to develop on a larger scale with big-name actresses, but Heather and Jennifer weren't interested in giving to other actresses the roles they had created for themselves. Jennifer's former talent agent, Kaye Popofsky, was pivotal in bringing them into Interscope, having left agenting to become a film executive there. Having been one of the few people who saw the original play in New York, she wanted to shepherd the project to the big screen with the girls attached to star and their vision intact. (She later left Interscope to found StepUp Women's Network, but remained connected to the project as an Associate Producer).

During this time, with the guidance of a director and studio executives, Heather and Jennifer developed and honed their script for over 18 months, only to get frustrated at the slow pace of the development process, as well as the number of people they were forced to answer to. They concluded that their film might be better served by being made in a grittier, more 'indie' fashion - the same way they created the play - and so when their option ran out in September of 1999, they moved on.

They got their rights back in turnaround, and soon teamed up with Eden Wurmfeld, who had line-produced the critical and commercial hit SWINGERS, among other independent films and documentaries. Wurmfeld said she knew she had a great film on her hands because "The script read like water....I could read draft after draft after draft, and I was wrapped every time."

The group then found Brad Zions, a former AOL executive who was in the market for a good project with which to begin a career in film production. After one read, KISSING JESSICA STEIN became the script he wanted to back. Not only was he taken with the characters of Jessica and Helen, Zions said he could truly relate to the frustrated artist in Josh Meyers.

Zions pledged to commit a full half of the film's budget: $500,000. This was a strong beginning, but the team still needed to raise almost half a million dollars piecemeal. This meant going to family, friends, friends of friends, and almost everyone in between to solicit investments to back the film. It was an intensely difficult time for the two actresses, whose artistic backgrounds could never have prepared them for their new role: saleswomen. "It was a nightmare," Heather says. "It seemed that all we did during that time was think about raising money. They don't teach you that in acting class."

To rise to the challenge, the actresses did what they knew how to do best: perform. With their producers, they held many staged readings of the screenplay, with a veritable 'traveling troupe' of actors - some of whom had been with them since the days of the play. During this time the team was faced with the simultaneous challenge of finding a director - a role that Westfeldt and Juergensen briefly considered but declined. The women were already wearing so many hats as writers, co-producers and performers, they were concerned that the added burden of directing and rallying troops on a set could sap them of the energy and focus they would need to deliver quality performances. They wanted to find a collaborator, someone who could bring as much boundless enthusiasm to the project as they did. They found this person in Charles Herman-Wurmfeld, an innovative theater director who had just completed an award-winning MTV documentary. He loved the script and was passionate about forging true collaborations with writers. He told the women, "Let me be the midwife to your baby, and help you realize your vision."

"Herman-Wurmfeld (who also happens to be Producer Eden Wurmfeld's brother) had a particular interest in the project because it was quite similar to his own experience coming out to his straight best friend while in his 20s. Herman-Wurmfeld's strong visual sensibility - especially teamed with cinematographer Lawrence Sher's dynamic camera work - was critical to making the dialogue-driven script cinematic and fluid. According to Juergensen, Herman-Wurmfeld brought "a wonderful visceral element where you always feel there's movement in the film."

With Herman-Wurmfeld attached, and the staged readings continuing, the team was slowly but surely raising the money to make their movie. At one point when it looked as though they would not have enough to "greenlight," or start production on time, Jennifer's parents actually liquidated a pension fund to make sure the film would not be irrevocably stalled (like all investors, they ended up getting that money back, with profit). These kinds of selfless acts of generosity came through time and again throughout the process, without which the film would never have been completed. (To get a sense of how many people lent a helping hand, just take a look at the lengthy "Thank You" list in the film's end credits.)

By the fall of 2000, exactly three years after their tiny off-off Broadway play's six-day run, Heather and Jennifer were finally shooting Kissing Jessica Stein on the streets of New York City. They shot the film in 23 days. Post-production lasted six months, with some of the editing done in New York, and the rest in Los Angeles. Early screenings of rough cuts of the film brought valuable audience feedback, as readings of the play had done years earlier. The filmmakers decided to do a brief one-day reshoot to address feelings from some audiences that the ending of the film was abrupt and unclear. These new scenes include several from the film's last few minutes, such as Helen getting ready for bed, Jessica reading a book in bed, and Helen in her new life. They were shot in several Los Angeles interiors dressed to match the rest of the film. The endless money-raising and searching for investors continued during this time to fund the extended editing process and reshoot.

The movie made it through this last breakneck period of post-production to be accepted - just in the nick of time -- at the 2001 Los Angeles Film Festival. The film's first public screening on Saturday, April 21, 2001 was thrilling not only for the filmmakers but for all their friends and allies who had supported them and cheered them on along the way. The capper came at the end of the festival, when the film won not only the Audience Award, but a Special Jury Award for Writing and Acting presented to Heather Juergensen and Jennifer Westfeldt. To top it off, a scout from Fox Searchlight had seen the film at the festival, and three weeks later the company purchased the film for worldwide distribution rights. The film would ultimately be released domestically on March 13, 2002.

after winning the LAFF audience award with Jennifer Westfeldt

The story of the two actresses determined to realize their dream was featured in national magazines like Premiere, Elle, Interview and Details, and most dramatically in an interview with Matt Lauer on NBC's famed Today Show, which reaches over 30 million people. A far cry from the film's tiny Off-Off Broadway beginnings!

In addition to being a favorite with audiences, the film was well received by critics, including Peter Travers of Rolling Stone and Owen Glieberman of Entertainment Weekly. The film has just completed a strong international release and is available everywhere on video and DVD.