Heroes of the Zeroes: Kissing Jessica Stein

Heroes of the Zeroes is a daily, alphabetical look back at the 365 best films of 2000-2009.

"Kissing Jessica Stein" Rated R 2001

“Kissing Jessica Stein’s” low-budget sheen boasted the qualities of a cable sitcom, but it always retained an observant emphasis on both its sit and its com.

Charles Herman-Wurmfeld’s 2001 comedy remains the best film spawned by “Sex and the City.” For this sharp-tongued story about emotional curiosity and the politics of passion, leads and co-writers Jennifer Westfeldt and Heather Juergensen drew on the words of a dead Austrian poet to muse about modern romance.

Newspaper reporter Jessica Stein’s (Westfeldt) biological clock is in the fourth quarter, so every date with a guy is a heave at the buzzer. Captivated by a personal ad’s Rainer Maria Rilke quote, Jessica answers the query placed by Helen Cooper (Juergensen), a bisexual art curator similarly dissatisfied with men.

“Stein” never sensationalizes, cheapens or simplifies either Jessica’s consideration of lesbian love or Helen’s frustrations with Jessica’s hesitancy to dive in. Their attraction to one another is magnetic and their quick-witted, verbal-sparring chemistry pure, but it’s atypical to both for different reasons.

Helen has never fallen so deep so fast, and Jessica is uncertain of her family’s response. (Tovah Feldshuh delights as Jessica’s mother, who, in a touching speech, assures her maternal love and asserts that greatness exists only out on a limb.)

The Rilke quote at “Stein’s” core gets at human compulsions toward emotional self-destruction. Whether Helen and Jessica’s time together becomes a lifelong bond is hardly the point, as “Stein” knows that love comes from a cumulative understanding of life's leaps made, not avoided.