Can a nice, straight Jewish girl from Long Island, frustrated with dead-end dates with guys, find love with a bi-curious downtown bohemian woman? That's the not-so-burning question at the center of Kissing Jessica Stein, and while the film doesn't offer an entirely expected answer, it gets there via a path littered with familiar landmarks. Stein's opening moments unspool as if director Charles Herman-Wurmfeld and co-writers/co-stars Jennifer Westfeldt and Heather Juergensen had spent time poring over Independent Romantic Comedies For Dummies. Playing the title character, a copy editor at a newspaper where heated arguments over verb preferences serve as water-cooler fodder, Westfeldt is shown home alone, making frequent trips to a refrigerator stocked only with Häagen-Dazs and leftover Chinese food, the dietary staples of quirky singles for nearly three decades. After experiencing a series of disastrous dates via a montage sequence, Westfeldt decides to answer a Village Voice ad from the "women seeking women" section, drawn by its inclusion of just the right Rainer Maria Rilke quote. Soon, Westfeldt and Juergensen begin fumbling their way through a lesbian romance, as coworkers and Westfeldt's tortured-writer ex-boyfriend (Scott Cohen) look on in wonder. While Stein never loses its devotion to formula or hides its talk-thick origins as an off-Broadway play, it takes a funny turn once it sets up its two leads: It takes a break from the obvious and relaxes enough to find its own voice. Westfeldt's caffeinated Jennifer Aniston routine may or may not translate into other movies, but here, both she and Juergensen generate considerable charm as their relationship develops from the tentative to the not-so-tentative. That charm doesn't last, unfortunately, once sobs and hug-inducing talks from Mom take over, and eventually Stein's habit of dodging its own issues grows frustrating. Juergensen and Westfeldt give their characters such supportive, difficult-to-shock friends and family, and so little capacity for suffering or inflicting emotional damage, that they might just as easily have made a film about trying on a new pair of shoes as a new sexuality.