In "Kissing Jessica Stein," the title character is a 30-ish Jewish everyday neurotic, a New York magazine copy editor who, pressured by family, society and herself, concludes it's time to get serious with a relationship.
Resorting to the personal ads, Jessica thinks she may have hit a potential winner with a wittily composed introduction that actually quotes Rilke. The only problem: It's in the "women seeking same" column. After much internal debate, Jessica finally makes the call and the leap into the previously unimaginable.
Most of what we might imagine, thankfully, is avoided in this well-written and even better-played look at postmodern romance that puts most romantic comedies in the shade. That the writers and the two main actors turn out to be one and the same is not really surprising; Jennifer Westfeldt and Heather Juergensen walk it like they talk it or, rather, wrote it.
"Kissing Jessica Stein" is one of those films whose pleasures are better discovered than described. But it's not giving too much away to say that when a frightened Jessica (Westfeldt) has her first hilariously uncomfortable meeting with Helen (Juergensen), a very together gallery owner, they turn out to have more in common than Rilke.
After some initial circling and swaying, the two embark on a relationship the right way: They become pals first and finally become comfortable enough where Jessica is able to, well, you know.
"Kissing Jessica Stein" has been compared to "Ally McBeal" and to Woody Allen comedies like "Annie Hall." That means it's not being relegated to the gay ghetto but is being recognized for its deft dialogue, its unusually well-drawn characters and its enthusiasm for addressing actual issues without becoming a message movie.