Kissing Jessica Stein (2002)

3 1/2 Stars (out of 4)

Kiss and Swell

By Jeffrey M. Anderson

You've never seen their faces before, so you're inclined to walk right by Kissing Jessica Stein and plunk your pennies down for something with big stars, something like The Time Machine, Dragonfly or A Beautiful Mind. But you'd be making a mistake. This little debut film by a couple of unknown New York charmers is one of the most highly entertaining films around, and -- better still -- one of the greatest romantic comedies of the past decade. That may sound like an exaggeration, but I've been pondering this for weeks now. I think we can agree that the high water mark for modern, post-Annie Hall romantic comedies thus far has probably been When Harry Met Sally... with a few memorable attempts in-between like Roxanne, Groundhog Day, Four Weddings and a Funeral, While You Were Sleeping and Chasing Amy. But the very nature of the modern romantic comedy genre makes these films feel like poofs of air, vanishing in time before they're even fully digested. Kissing Jessica Stein is the first one in ages that feels like it's going to stick around.

Jessica Stein (Jennifer Westfeldt) is an adorable blond Meg Ryan-ish New Yorker, fraught with anxiety and working as a copy editor for a major New York publication. She comes complete with a Jewish mother and a perpetual single-ness -- keeping her from finding the right guy. We see her on a series of bad dates with would-be writers with questionable vocabulary skills and accountants with a penchant for splitting the bill according to how much food each participant ate. One day a co-worker reads through the Village Voice singles ads and comes across a perfect notice for Jessica -- filled with poetry and proper word usage. But, oops! It's in the women-seeking-women column. Intrigued, Jessica decides to answer the ad anyway. And so she meets the lovely Illeana Douglas-ish Helen Cooper (Heather Juergensen), a bisexual artist, looking for a full-fledged sexual relationship. But even though the girls click on a personal and emotional level, Jessica still isn't too sure about the sex. What's more, Jessica's co-worker and former boyfriend (Scott Cohen) seems to be sending mixed signals, which only confuses things.

Westfeldt and Juergensen wrote the screenplay for this intriguing scenario -- based on their play Lipschtick -- and Charles Herman-Wurmfeld directed. It's full of that gloriously sunny world-is-full-of-possibilities atmosphere established by Annie Hall and When Harry Met Sally... where every conversation in front of a picturesque New York location or in a wondrous apartment comes weighted with the Meaning of Life. Westfeldt and Juergensen are smart enough to concentrate on character before anything else. Their own personalities come full-force, enough to guarantee them sparkling careers as movie stars. And the supporting characters pop as well, notably Tovah Feldshuh as Jessica's mother and Jackie Hoffman as Jessica's best friend. (The movie's biggest flaw is perhaps Helen's gay friends, who aren't onscreen long enough to develop past the usual queeny clichés.)

On top of it all is that sparkling dialogue that would make anyone from Preston Sturges to Paul Rudnick sit up and take notice. One random scene from my memory has Jessica and Helen in the back of a cab plotting to go away together for the weekend and blow off dinner at Jessica's mother's house. They call the mother on Jessica's cell phone to tell her, but over the course of about two minutes -- all dialogue -- their plans are shattered. Cut -- they appear at the mother's house for a long, awkward dinner. Remember back to the time before you knew who Meg Ryan or Hugh Grant or Sandra Bullock was. Remember that you went to the movies and discovered these stars and how exciting that felt. Now grab hold of that memory and go see Kissing Jessica Stein. Jennifer Westfeldt and Heather Juergensen will not let you down.