iTunes Movie of the Week: Charles Herman-Wurmfeld's KISSING JESSICA STEIN (2001)

The romantic comedy. It's dicey territory. For every genre-defining feel-good flick, there are literally hundreds of sub-par, star-studded vehicles. What we're getting at is, good rom-coms are hard to come across, which makes KISSING JESSICA STEIN all the more special.


Jessica Stein is a sensitive but neurotic New York journalist who also happens to be at the end of her emotional rope. Her brother’s engaged, her best friend’s pregnant, she hasn’t dated in a year, and she can’t sleep. After an optimistic but nightmarish dating spree, she happens upon an intriguing personal ad... whose only drawback is that it’s in the “women seeking women” section. On a daring whim, she decides to answer it, and meets funky downtown hipster Helen Cooper. A lively evening of banter, connection and heated debate culminates in a kiss that confounds and intrigues even the reluctant Jessica. Kissing Jessica Stein is a modern romantic comedy that breaks all the rules, blurring the lines between friendship and romantic love, and finding the funny, surprising and ultimately poignant overlap between the two.

KISSING JESSICA STEIN has an impressive 86% score on Rotten Tomatoes. Here is what some top critics had to say at the time:

"Likable romantic comedy KISSING JESSICA STEIN rises above its sitcom premise by virtue of its charm, warmth and clear-eyed vision of the perils of any relationship." – David Ansen, Newsweek

"I would have even kissed the screen upon which Jessica's giant image is flung, but there were security guards between it and me, and a reputation, as well as a career, to consider." – Stephen Hunter, The Washington Post

"The movie makes of this situation not a sex comedy but more of an upscale sitcom in which both romantic partners happen to be women." – Roger Ebert, Chicago Sun-Times

Fun fact: the movie also features Mad Men's Jon Hamm in a supporting role – he has been dating KISSING JESSICA STEIN's star and screenwriter, Jennifer Westfeldt, since 1997. Score 1, Jessica Stein, then. For more info, visit the Official KISSING JESSICA STEIN site!

Here's the trailer, for your viewing pleasure:

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