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This article originally appeared in The Jewish Journal of Greater Los Angeles and is reprinted with permission of the author. Visit www.jewishjournal.com.
When Jennifer Westfeldt and Heather Juergensen shared bunk beds at a 1996 Catskills theater workshop, they swapped stories about Mars-Venus angst.
Westfeldt, an Upper West Side Jew, was breaking up with her college boyfriend and dating for the first time. Juergensen, a downtown bohemian, was juggling three guys and feeling guilty. Their girl talk led to a 1997 play and a movie, Kissing Jessica Stein, in which two women escape heterosexual hell by dating each other.
The frothy if sometimes clichéd romance, a lesbian take on "Sex and the Single Girl," puts a new spin on the saga of the befuddled single woman (Annie Hall meets Bridget Jones' Diary). Stein (Westfeldt) is a prudish Upper West Side Jewish copy editor with a mean ex-boyfriend and an overbearing mom (Tovah Feldshuh), who thinks she's too picky. On a whim, she answers the perfect personal ad--except it's in the women-seeking-women section. She meets Helen (Juergensen), a promiscuous, "bi-curious" Chelsea gallery owner. The comedy veers into bedroom farce when Jessica's mom invites Helen to Shabbat dinner.
Westfeldt dates her relationship woes to her childhood in a WASPY Connecticut town. "My mom would say, 'Why don't you date a nice Jewish boy,' and I'd say, 'Because this one's ugly and that one's crazy,'" she recalls. "That's how many Jewish boys there were around."
When the family shleped into Manhattan to B'nai Jeshurun services--today the ultimate singles' synagogue--led by Westfeldt's esteemed great-uncle, the late Rabbi Marshall Meyer, mom pointed out cute guys for young Jennifer to check out. The memories inspired a "Stein" Yom Kippur scene in which Jessica's mother is so obnoxious, Stein finally blurts: "Will you shut up? I'm trying to atone!"
Though the characters' dating histories are loosely based on the authors', Westfeldt and Juergensen, both "30-ish" say they've never dated women (including each other). But Westfeldt insists the concept isn't far-fetched. "While writing the story, we interviewed dozens of women, straight, gay, crossed-over, crossed-back," says the actress. "Plus, we all have these wonderfully close women friends, and lots of us wonder, 'What if my girlfriend made the perfect b.f.?'"
The film also features hilariously exaggerated versions of the authors' crummiest dates: The lech who suggestively rubbed his chest; the nerd who meticulously split the check; the malaprop-prone doofus who declared he was a "self-defecating guy." "Like Jessica, I'm something of a wordsmith, so that was absolute torture," says Westfeldt, a Yale theater grad.
Less icky was rehearsing her first girl-on-girl smooch, courtesy of Juergensen, though "We were both nervous," she confides.
Juergensen, an earthy lapsed Protestant, agrees: "I knew there wasn't a man attached to those lips, but eventually our professionalism kicked in," she says.
After their 1997 play version of Kissing, Lipschtick, created a deafening Hollywood buzz, Westfeldt and Juergensen were barraged by studio offers. "Our play closed on a Saturday, and by Monday my agent's phone was ringing off the hook," says Westfeldt, who previously starred in the ABC sitcom Two Guys, a Girl and a Pizza Place.
"It was the classic Hollywood bull-machine; people were like, 'We need to sit down with these girls and option their play, but they hadn't seen it or read it or met us.'" Eventually, the actresses sold the script and completed more than 100 rewrites, but decided to go independent when their dating-hell flick turned into development hell. Westfeldt's favorite indie film moment: The time they shot in a cab with the sound guy locked in the trunk.
The filmmakers' perseverance paid off when they sold Stein to Fox Searchlight and won the audience award for best feature at the 2001 Los Angeles Film Festival. Observers compared them to Matt Damon and Ben Affleck, who also jump-started their acting careers by writing a scrappy independent film (1997's Good Will Hunting).
Since then, the actresses have encountered criticism from people who charge that Stein suggests sexuality is a choice. "But we had no interest in a political agenda," Westfeldt says. "We just wanted to show how diverse we all are."
That's why she thinks Stein would have pleased her famously progressive great uncle, who welcomed gays at B'nai Jeshurun and chastised the Conservative movement for refusing to ordain homosexuals. "The movie is all about tolerance and acceptance," Westfeldt says.
During a lighter moment, she notes that viewers still assume she and Juergensen are lesbians (they actually live with their respective boyfriends in Los Angeles). "People ask us, and we say no," she says, with a laugh. "But we're almost embarrassed to admit we're not."