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There’s a scene in the middle of “Kissing Jessica Stein” in which the title character finally ‘fesses up. Her best friend, about eight months pregnant and fittingly impatient, has been grilling Jessica for weeks about who she’s been seeing. Jessica is cornered, squatting on her sofa, so tightly sprung she’s about to climb the bookcases. She’s got a throw pillow in a death grip when she spits out the truth: She’s been dating another woman.

Are you freaked out? Horrified? she asks. Are you disgusted by me?

“Are you kidding?” her friend responds, mouth agape. “I’m impressed!”

That is how the movie “Kissing Jessica Stein” works. It never gives the answer you quite expect.

The creation of two actresses who became writers, “Kissing Jessica Stein” is something of a sheep in wolf’s clothing. It’s got a low-budget, indie pedigree, to be sure. It was also groomed by Hollywood and has the slick production values to match. It’s being distributed by Fox Searchlight, a company known for shepherding idiosyncratic strays into the mainstream. In this case, it’s a quirky portrayal of how falling in love with the wrong woman can change your life.

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“Kissing Jessica Stein” might have been controversial once, back when two women kissing in an R-rated movie could still be considered controversial. Maybe it’ll still tweak the sensibilities of some uptight folk--gay or straight--who go to movies looking to be offended. There was, in fact, a moment during the gay film festival Outfest last summer when things might have turned ugly. After a screening, a woman asked writer-actresses Jennifer Westfeldt and Heather Juergensen if they didn’t see the danger in creating a character who slips her sexual orientation off and back on like a cardigan sweater.

The two handled it with aplomb.

“The gay women we talked to didn’t identify with Jessica Stein,” one of them said, “but they’d dated Jessica Stein.”

Tidy labels don’t fit “Kissing Jessica Stein.” Its stars, Juergensen and Westfeldt, consider themselves actresses and writers. Their characters dance up and down the continuum of sexual orientation. The film itself is a gay movie about a character who isn’t gay. There isn’t a pigeonhole big enough.

“I guess they’ve just recently elongated the gay-lesbian-bisexual-transgendered-and-questioning community. And questioning!” lilts Westfeldt, cross-legged on a slipcovered chair in her sunlight-filled Los Feliz apartment. “Did you not hear this? It’s de rigueur! You have to say, ‘and questioning.’” she continues, gesturing with a flip of her hand. “That, to me, is exactly what we’re talking about.”

Westfeldt has the look--and she knows it--of the quintessential TV girlfriend, a lovely but uncomplicated face framed by thick, amber-blond hair. After acting professionally since she was a teen in regional theater, she slipped right into TV pilots when she moved to Los Angeles in 1997. Casting agents found her perfect for the understanding girlfriend from the Midwest or the ex-husband’s new love interest.

Juergensen is striking in a different way: tall, dark hair, fair skin, blue eyes. As a high schooler in Brooklyn, she had a thing for acting but found the pursuit too daunting, until she faced a career in advertising. She enrolled in acting classes and joined a theater company in 1993, and eventually produced her own one-woman show, “Letters to an Older Man.”

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The two hit it off at a 1997 theater lab in the Catskills, the kind that encourages getting things down on a page then up on a stage. Westfeldt was supposed to start a recurring role (as a girlfriend) on the ABC TV series “Two Guys, a Girl and a Pizza Place,” but a six-week delay at its start gave the women a chance to build on their momentum. Westfeldt came back to New York, they booked six nights at a theater off-off-Broadway and started writing.

The idea was an evening of scenes on the perils of dating. (Traces of this survive in “Kissing Jessica Stein” as a two-minute montage.) Among the characters were two straight women, fed up with men, who meet in a day spa to negotiate becoming lovers. It was broad humor, an over-the-top “what if” scenario. They got more and more interested in that one kernel, but had to mount the play before they could explore the deeper facets of that relationship. Says Juergensen, “We all say what if, what if? But really, what if?”

Still, that aspect of the show, called “Lipschtick,” generated immediate buzz and landed them meetings in Hollywood. As they started to write a more focused movie script, they knew one thing: They weren’t giving up the roles that got them the attention. Jessica (Westfeldt) is a frustrated artist who feels deeply alone, in a hysterical, high-strung way. Helen (Juergensen) is a downtown Manhattan hipster whose nonchalance about her bi-curiosity belies a dissatisfaction with her relationships. “We created these characters as actresses, and we identified with them so much,” Juergensen says. “You just don’t want to give that to someone else.”

The script was quickly optioned by Interscope. The whole Hollywood development process--the antithesis of “get it on the page and up on the stage”--was a crash course in movie structure, screenwriting, marketing. Westfeldt nods toward her computer and jokes about 300 different versions of the story; and then it seems she isn’t really exaggerating. Adds Juergensen, “It was like dog years.” It came down to this: Interscope wanted to make a Hollywood comedy, something like “In & Out.” The director--actor-director Saul Rubinek (“Jerry and Tom”) was attached at the time--wanted a more edgy, art-house approach. The women wanted it both ways. Can’t we retain the accessible comedy, but keep the un-Hollywood ending and the other quirky elements? they asked.

“They said, ‘Yeah, that’s called a ‘tweener,’ and we don’t want to make that movie,” recalls Juergensen. “‘That makes us nervous because the theory is you lose both audiences.’”

Of course, you could get both audiences--the indie movie lovers and the mainstream comedy crowd. “The Full Monty” (1997) did it, for instance, as Westfeldt was reminded each morning as she drove onto the Fox lot. “Every day there was this banner for ‘The Full Monty’ that said ‘“The Full Monty” has now made $200 million!’ Every day I’d come in and the number, like at McDonald’s, would be changing.”

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“The Full Monty” became their inspiration. It proved that a laugh-out-loud comedy doesn’t need a big budget and that a strong story doesn’t depend on stars. And it proved that comedy and poignancy could peacefully coexist.

But to pull a “Full Monty,” Westfeldt and Juergensen needed to find the right relationship.

When Interscope’s option on “Lipschtick” expired in 1999, the rebound girl was practically living next door. Eden Wurmfeld, who’d been the production manager on the indie hit “Swingers” (1996) and produced “See Jane Run” (2000), had known Westfeldt since their early 20s and, coincidentally, was living just down the street in the Fairfax district.

She’d read the various drafts of the stage play and the script, and loved the story.

“It was like when you secretly have a crush on someone, but you don’t want them to know,” Wurmfeld says. “They were at the studio; they were married to someone else.”

The missing piece was a director, someone who could drop the auteur mantle to collaborate with Westfeldt and Juergensen--there would be no throwing the writers off the set in this production. That ruled out a lot of people. Plus, directors who’d made indie hits weren’t interested in shooting a $700,000 movie for no pay anymore.

The man for the job, it turned out, had been sleeping on Wurmfeld’s couch: Charles Herman-Wurmfeld, her brother, a film and theater director who is also a serious student of acting.

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For him, “Kissing Jessica Stein” as a big opportunity with deep personal resonance. When he was 21, he fell in love with his best friend, a man who ended the relationship six months later because he wasn’t gay. That was just the beginning of a rocky coming out, during which he took his mother’s maiden name after a falling out with his father. (Rifts healed, and he now uses both names.)

While Juergensen and Westfeldt had done a lot of interviews, Herman-Wurmfeld drew on experience. He advocated for the new title as Jessica evolved into the clear protagonist. He helped shape Helen’s character and the arc of the relationship. An early scene shows Helen snort down a stiff drink after a quick sexual encounter with a man. And at the end, it’s Helen who demands more of the relationship than Jessica can really give.

“The conscious choice for us was not just to tell one story, but hopefully many,” Westfeldt says. “If the women did end up together, it would be like: two women who start out at the top of the movie seemingly straight, try this experiment for all the wrong reasons, and both have the exact same revelation at the exact same moment.” Instead, the ending is left somewhat open. There is a suggestion that Jessica may rekindle a relationship with an ex-boyfriend, Josh (Scott Cohen). But there are those, Herman-Wurmfeld says, who read the tale as her first step in a longer coming out.

Shannon Kelley, director of programming for Outfest, said “Kissing Jessica Stein” gets beyond girl-meets-girl. There’s been a push to establish a lesbian identity in American films, he said, but “Kissing Jessica Stein” shows that “we’ve come to a point where the culture is established enough to play around with it.”

Certainly the archetype of movie lesbians has been at best humorless and more often tragic. The string of ruined lives that began with “The Children’s Hour” (1961) still hasn’t ended if “Mulholland Drive” (2001) is any indication. Even characters who find lasting love are subject to prescribed amounts of suffering, as in the critically acclaimed “Aimee & Jaguar” (1999) or “All Over Me” (1996).

But while Helen and Jessica don’t remain lovers, they’re not left damaged. In the end, Jessica has become a little gay for a period of her life, and she’s much better for it. “Each of them is shattered and reassembled,” Kelley notes. “But it’s the fact that they’re reassembled that makes it different from other films.”

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The film drew near unanimous praise at film festivals around the country, including the Chicago International Film Festival and Jewish film festivals in Boston and Louisville, Ky. Last month it won the Audience Award at the Miami Film Festival. When it played the Los Angeles Film Festival last April, Variety’s Lael Loewenstein wrote in her review, “A fresh take on sex and the single girl, this buoyant, well-crafted romantic comedy blends pitch-perfect performances with deliciously smart writing.”

At the Los Angeles festival, it won the Audience Award for best feature film, a special jury award for acting and writing, and the biggest prize of all: a distributor.

The “power breakfast”--as Herman-Wurmfeld still has it recorded in his Palm Pilot--was at an outdoor cafe at a Century City hotel. He and the writers and a film broker sat around a huge round table with executives from Fox Searchlight, the company that had distributed “The Full Monty.”

“It was like sending your child to boarding school,” he said. “You want to make sure the teachers are smart and sensitive and understand your kid. You want to ask all the right questions, but you don’t want to offend them in any way.”

Westfeldt and Juergensen were excited but wary. They’d met with other studios that had wanted to tinker with the film for theatrical release.

Softly but directly, Westfeldt asked Fox Searchlight President Peter Rice: “So what do you foresee having to change in this film?”

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Recalling his answer, Westfeldt impersonates Rice’s confident voice, his clipped British accent: “We will release this film, literally, as is.”

The few things about the film that changed largely did because the world changed around it. Nine skyline shots of New York were replaced after Sept. 11. The film screened at the Toronto International Film Festival only days after the terrorist attacks, and it was evident that the shots were causing the audience to drop out of the story.

They substituted shots that were more specific to their story--ones of Chelsea, where Helen works at a gallery, or of Central Park, where Jessica goes running. The new shots, like “Kissing Jessica Stein” as a whole, capture a carefree energy and optimism that are less evident in New York now, says director Herman-Wurmfeld. For him, the film is “the last piece of a moment in time in New York.”

But there’s a certain kismet in the changes too. In one of the shots they added, a taxi is driving past. On its side is a sign advertising a new Broadway musical, “The Full Monty.”

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Robin Rauzi is a Times staff writer.

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