A pair of playwrights take their girl-meets-girl comedy Kissing Jessica Stein out to the movies.

It’s gotten to that point. Even Meg Ryan is sick of romantic comedies, joking on the eve of her latest, Kate & Leopold, that she wished there were a support group for its stars. But when the Michael Jordan of love stories wants to retire, what’s Hollywood to do? Infuse the genre with some new blood.

Enter actress-playwrights Heather Juergensen and Jennifer Westfeldt, whose movie, Kissing Jessica Stein, hopes to restore freshness to the stale boy-meets-girl scenario. How? By exploring the final frontier: not sex and the single girl but rather sex with the single girl next door.

In the Fox Searchlight film, out March 13, Westfeldt (Two Guys, a Girl and a Pizza Place) plays the titular Stein, a neurotic New York City copy editor and self-described ”Jewish Sandra Dee” who, burned out from a series of disastrous dates, answers a Woman Seeking Woman ad placed by Helen, a bi-curious hipster played by Juergensen (primarily an Off Broadway actress). With charming awkwardness, the two begin a unique relationship (by romantic-comedy standards at least) that includes Jessica revealing her straight-girl skittishness by bringing Helen several pamphlets of various lesbian sex accoutrements — on the second date.

The actresses, who admit to being between 28 and 31, met at a writing-performing workshop. They adapted the movie from their original 1997 Off Broadway play, Lipschtick, which they based on their own frustrating dating experiences and anecdotes they culled from women they knew. (For the record, both women are straight, though Westfeldt concedes she is ”sometimes loath to admit” it.)

After the screenplay was sold to Gramercy Pictures in 1998, the project went the way of most Jessica Stein dates — nowhere. In December 1999, the two bought back the rights, borrowing $750,000 from friends (most from Internet mogul-turned-movie producer Brad Zions) and went to work. ”We got hungry,” says Juergensen. ”We kept seeing stuff on Friends and Ally McBeal that was getting uncomfortably close.”

While dabbling in lesbianism is now a ratings-grabbing plotline on TV (including a March 11 teen-lesbian episode on ABC’s Once and Again), it’s still a brave new world for Hollywood. (1994’s Go Fish is probably the most successful lesbian love story, and it grossed $2.4 million.) But the subject matter didn’t deter potential investors nearly as much as the lack of star power. ”When we were talking to people about the film, what we heard more of was ‘Romantic comedy with no stars? Forget about it,”’ recalls producer Eden Wurmfeld (Swingers), sister of KJS director Charles Herman-Wurmfeld.

Once the film won the Audience Award at the Los Angeles Film Festival, there was no shortage of suitors. Fox Searchlight eventually snapped it up for $1 million and is now banking on single girls to turn Westfeldt and Juergensen into the distaff Ben and Matt. To build buzz, the movie has played at 11 film festivals nationwide.

Westfeldt and Juergensen, who expect to collaborate again in the future, hope more than chicks check out their flick. ”There is no way [Kissing Jessica Stein] could be a Meg Ryan movie,” says Westfeldt. ”But we knew if it could feel like a Meg Ryan movie turned on its ear, then we would reach a lot of people.” Maybe even Meg.

Kissing Jessica Stein
  • Movie
  • 96 minutes