Combining the roles of director and writer happens all the time in moviemaking. An argument might even be made that a disproportionately high percentage of good movies are made by writer-directors. But writer-actor combinations are far less frequent and Kissing Jessica Stein stars not one but two actors who are also responsible for the screenplay. It’s a maiden voyage for both Heather Juergensen and Jennifer Westfeldt on screen and behind. The results are enhanced by their fresh their point of view even while their inexperience is apparent in the weaknesses of the screenplay.
Kissing Jessica Stein started as a stage play called Lipschtick which the same team wrote and starred in off-Broadway. Director Charles Herman-Wurmfeld (also a novice–this is his second film) has opened up the play with a handful of outdoor scenes and he has interspersed travelogue-like shots of New York, but the somewhat confining interiors dominate and the film is dialogue-driven in a stagy fashion. Still, the writers have good ears for dialogue and are quick with inventive quips which carry the action along. (The tight production budget is also noticeable in the occasionally poor sound quality.)
Jessica (Westfeldt) is a late twenties single from an upper middle-class Jewish family. Despite being attractive, educated, intelligent, and employed, she’s not been successful at establishing a relationship and resorts to the personal ads. As a lark, she responds to one from another woman whose ad pitch was appealing. Helen Cooper (Juergensen) is assistant director of an art gallery and a bisexual taken to doing her yoga in front of a statue of Ganesha. Her liberated ways contrast with Jessica’s more traditional constraints. Over time, and with great patience from Helen, acquaintanceship blossoms into friendship and friendship blossoms into an affair.
A legitimate lesson from the experience of the gay/lesbian community is that people don’t chooseto be gay and, therefore, it might be concluded that this relationship is founded on shaky ground. Cleverly, the writers have that very point of view expressed in the film by a gay male friend of Helen’s. In reality, while it may not be a matter of choice, the range of sexual orientation along the homo/hetero continuum is probably a lot more diverse than many gays acknowledge. (It’s not uncommon to hear allegations that self-labeled bisexuals are just homosexuals who can’t face up to it.) In any event, the affair these two women have seems perfectly credible in the film, whatever its degree of political correctness.
Josh Meyers plays Scott Cohen, Jessica’s boss and one time boyfriend. It’s a bothersome flaw that the history of their relationship is not better developed in the film. Knowing why it fell apart might have added to a better understanding of Jessica’s motivations, beyond the stereotypical hounding of mother and grandmother to get married. It also would surely have bolstered the weak resolution of the story which wants to lead the heroine through a lesbian affair, but seems anxious to return her to the more mainstream alternative.
Juergensen is quite perfect as Helen–independent, self-aware, realistic and unaffected. Westfeldt, on the other hand, is charming, but buries her character is what has become the trademarked set of mannerisms that trace back to Diane Keaton’s Annie Hall–a sort of cutesy, put-on self-deprecation withbreathy little gasps before a word comes out, lifted eyebrows, and other recognizable hallmarks of the type. It’s become an established speech pattern amongst high school girls but seems somewhat precious in an adult about to hit thirty.
Still, there are plenty of lines that generate laughs (with only occasional duds) and a breezy lightness that Herman-Wurmfeld manages to sustain until the unconvincing resolution. Kissing Jessica Stein will doubtlessly please many, so long as expectations are not more than a notch above sitcom standards.