That charm is very much by design. Co-leads Jennifer Westfeldt (as Jessica) and Heather Jeurgensen (as Helen) developed their characters in a theater workshop environment that led to the play Lipschtick (a much more appropriate title given the ethnicity and lipstick metaphor flying about). So when Charles Herman-Wurmfeld signed on for his feature-length debut, it's as if the heart of the story was already in place. And while this film sounds like the story one woman looking for love, it's really the story of two. The difference is key, because as Kissing Jessica Stein so smartly, wittily and sincerely points out, it takes all kinds, and when it comes right down to it, does it really matter who we find as our soulmate, as long as they make us happy and push all our buttons?
Before continuing, it would be foolhardy not to admit that a lot of the charm of Kissing Jessica Stein is that, in Westfeldt and Jeurgensen, a mainstream audience has two very accessible actresses to watch. For as the play's title partially suggests, they are members of that controversially dubbed sub-group, "lipstick lesbians"; their sexual politics don't seem nearly as passionate as their fashion sense. (In one cab-ride scene, Jessica alternates a cell-phone call to her Jewish mother with admiring Helen's leather pants: "I am so borrowing this!") It's almost a guilty pleasure after seeing such heavy-handed, mid-90s films as Go Fish and Bar Girls. Kind of like watching the wit and snap of Will & Grace after gritting your teeth through those waning days of Ellen, even though you had to see one before the other. No question, these women are dressed to the nines, their eyeliner on target, their hair coiffed just so.
And yet, just when you'd assume that Kissing Jessica Stein is tailor-made for the hetero scene, that character development gives the viewer -- any viewer, hopefully -- some dimension to enjoy. For unlike its predecessors, this isn't really about finding the right woman per se. It's about finding love and the twisted road that we sometimes have to take to get there regardless.
Kissing Jessica Stein starts out hilariously with the concurrent love lives of Jessica and Helen, who of course would seem like a mismatch at first glance. Jessica, with Westfeldt taking a few pages from Diane Keaton's Annie Hall playbook to great effect, is a classic neurotic New York Jewish girl. As a copy editor, she's a stickler for detail in everything including the many loser men who pass through her blind-date booth (a cliche that is carried off surprisingly well). Heck, we all cringe at the "writer" who enthuses over the "endorfmans" that kick in when he works out! But as her ex-boyfriend and current boyfriend Josh (Scott Cohen) points out rather ruefully over dinner with friends, maybe it's not the men. Maybe it's her. And maybe he's right. So she's got issues.
Helen's more adventurous, more funky as the downtown hipster art gallery assistant, juggling as many men as there are shades in her lipstick application -- as telling and cute a metaphor as I've seen in a romantic comedy. So, initially encouraged by her gay friends, she decides to do what any hip New York woman would do: she decides to seek adventure in a lesbian liaison with a personal ad and winds up with her fair share of scary voice mails. Jessica hears the ad read to her and initially is intrigued -- they both seem to like the same writer -- realizes it's a woman, then decides to answer the ad for the hell of it.
So they meet, there's awkwardness, they become attracted, there's more awkwardness, and then they try to establish a romance, and then there's even more awkwardness. And when they finally "hook up" -- in a scene that gives into (thankfully) zero hetero-male fantasy wish -- well, then the real awkwardness ensues. Because as much as they seem to "click," as Jessica says -- using that word we all grope for in a mate -- the core issues of compatibility bubble to the surface.
Which is where Kissing Jessica Stein becomes truly a fragmented story, for like so many relationships in real life, the story doesn't go according to the preconceived notions of a happy ending. There are other niggling problems, too. One of Helen's gay friends suddenly disapproves, accusing her of being fashionable. When they do finally "come out" as a couple, Helen's friends and family -- particularly her typically disapproving mother (Tovah Feldshuh) -- are too easily approving.
But the struggle to the finish line of this film becomes all too understandable, because that's where, as in relationships in general, it's never very easy.