Kissing Jessica Stein 2001

"To a longtime single woman, the prospect of yet another movie about dating must seem as unappealing as the promise of yet another date. It’s easy to imagine: after a small investment, followed by a long evening, we retire to our corner, nursing disappointment and wondering if the problem lies with us. 

So I’ll act like your mother and say, give Kissing Jessica Stein a try. You’ll really like it. The writing team of Heather Juergensen and Jennifer Westfeldt, who also star, come from the theater world, where they nursed their script through a brief Off-Broadway run and three years of development. Their effort pays off in laugh-out-loud lines, adorably ditsy but heartfelt performances, and sparkling, bittersweet dialogue that cuts to the chase of the modern girl’s dilemma.

We first encounter Jessica (Westfeldt), a New York journalist, at Yom Kippur services in a Scarsdale synagogue, where her mother (the inimitable Tovah Feldshuh) and grandmother are arguing about whether the man in the next stall is good enough for her. Cut to the newsroom, where she toils beneath the curmudgeonly glare of her boss and former college boyfriend (Scott Cohen), and to a series of hilarious brief encounters with inappropriate men. Meanwhile, fetching hipster Helen (Juergensen), a Chelsea gallerist who blends lipsticks and juggles three (male) lovers, decides that a change is in order. ‘Today sexual preference, tomorrow henna tattoos,’ a gay friend quips. But she places an ad (in the Village Voice!) looking for some female action, and Jessica responds.

The rest is a story of girl getting girl, and then wondering what to do with her. The writers strike a few false notes: in this newsroom, at least, people don’t argue at length about the meaning of adjectives, and bisexuality is no great cause for consternation… But beneath the satire lies a well of tenderness, more moving in its confusion than the pat answers to singledom that Hollywood usually offers." — Leslie Camhi, Village Voice