Seeking Same

by Anna Pulley


Kissing Jessica Stein, written and co-produced by the film’s leading ladies, Jennifer Westfeldt and Heather Juergensen, is an independent romantic comedy that revolves around Jessica’s (Westfeldt) neurotic and oft-times hilarious, stuttering triumphs and defeats in the world of dating. Based on the off-Broadway production Lipshtick (also by Westfeldt and Juergensen), this film is a kind of straight girl’s guide to novice lesbian dating in New York City. The Manhattan setting contributes to the cosmopolitan sensibility of Jessica’s dating dilemmas, which echo the larger professional twentysomething problems of dating in New York capitalized by HBO’s “Sex and the City” and numerous others, from Gold Diggers of 1933 to Annie Hall to Maid in Manhattan. The DVD tagline, “There’s More Than One Kind of Sex in this City” directly parallels this notion of New York women’s vulnerability when it comes to finding “a few good men” or in Jessica Stein’s case, one good woman. As she laments, “I don't believe there's just one person. I think there are, like, seven.”  The anonymity of the large New York backdrop in part allows Jessica to experiment with her sexuality in ways that would be denied to her elsewhere. With a little help from Rainer Maria Rilke, whose quote from Letters to a Young Poet sparks a desire in her to “live the relation to another as something alive,” Jessica embarks on a disastrous series of dates with such hopeless characters as the-not-yet-out-gay guy, the nipple-stroking-big-teeth-misogynist, and the unforgivably-geeky-accountant before finding Helen, a hip art gallery director, who provides some much-needed GHB to Jessica’s neurotic cocktail.


 
Words are an essential motif in the film, both their meanings and implications. Jessica is a copyeditor for a major newspaper, whose second line of dialogue is enlightening a co-worker on the definition of “nonplussed.” She’s especially critical of malapropisms in the bad-date montage, where one guy describes himself as “self-defecating.” She decides to give Helen a shot only after she uses the word “marinate” in a context outside of food preparation. Josh, her ex and future boyfriend, is a struggling writer. Jessica’s obsession with words, (and on a broader scale, perfectionism) follows her into the bedroom, where she comes equipped on her second date not with a U-Haul but with a panoply of lesbian sex pamphlets and literature on the topic. “I was surprised to learn that lesbians accessorized, I didn't know that.” Indeed, Jessica’s approach to sex is reminiscent, in Roger Ebert’s words, “of a homeowner considering the intricacies of a grease trap.” Her hyper-scrutiny is one of the funniest aspects of the film because she’s just as hard on herself as she is on her potential suitors. For instance, when Jessica is telling Helen why her last relationship didn’t work out, she says:
 
He just wasn't funny, you know? That's always been my problem, I think. Not smart or not funny. Or not smart and not funny. Or smart, but in a totally unappealing way like funny stupid or funny dopy, rather than funny witty, or funny irony or funny goofy. Or, you think they're smart- and then you realize that they're not- and that's funny. But funny…tragic. And then, if you're lucky enough to find someone who's the right kind of smart and the right kind of funny, usually they're just ... kinda ...
Helen: Ugly?
Jessica: Ugly, exactly. Oh my god, is that awful?
Helen: No, not at all. Ugly doesn't do it for you. That's okay. See me, I'm kinda into ugly ... But only if it's sexy-ugly. 

The phrase sexy-ugly, which has gained considerable popularity since its inception, is coined here, adding a new spin on unconventional desire to the dating lexicon.
 
When push comes to shove, Jessica’s girl-on-girl narrative turns out to be as lucrative as her fact-checking zeal with the Tribune, which she also ditches at the film’s end to pursue a career as an artist. Her lesbianism stems from a kind of heterosexual disenchantment, which dwindles to a halt after about six months, but this doesn’t detract from the film’s light-heartedness and angsty Annie Hall-type diatribes. And really, when does one go to the romantic comedy section in order to learn the profound nature of human existence? Instead, Kissing Jessica Stein offers us frustration in all its glorious forms—sexual, artistic, familial, and societal. Jessica’s mother Judy (whose role was written specifically for Tovah Feldshuh) is a particularly amusing element to the film’s frustration dynamic. She is constantly trying to set Jessica up with boring, balding IBM types despite her daughter’s protestations. For Judy, any man alive enough to accept a dinner invitation is brilliant, gorgeous and perfect for Jessica. Judy: “How was I supposed to know he was in rehab?” Jessica: “I don’t know, mom—wan, pale, track marks?” Judy’s non-existent standards are in polar opposition to Jessica’s perfectionism, which adds another comedic yang to the story’s yin.
 
In the end, Jessica ends up kissing the most obvious person, while Helen goes on to pursue other lipstick lesbians who are “a little more gay” than Jessica ever could be, and New Yorkers resume their sordid affairs with each other and with the city itself. Everybody wins.