Kissing Jessica Stein

  • 2002
  • Movie
  • R
  • Comedy, Romance

Two heterosexual girly-girls decide to give lesbian love a try in this cuddly romantic comedy. A veteran of the dating wars, high-strung, strenuously quirky New York City copy editor Jessica Stein (Jennifer Westfeldt) is beginning to wonder whether she'll ever meet Mr. Right. Everyone says she's too picky — especially her mother (Tovah Feldshuh) and...read more

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Reviewed by Maitland McDonagh
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Two heterosexual girly-girls decide to give lesbian love a try in this cuddly romantic comedy. A veteran of the dating wars, high-strung, strenuously quirky New York City copy editor Jessica Stein (Jennifer Westfeldt) is beginning to wonder whether she'll ever meet Mr. Right. Everyone says she's too picky — especially her mother (Tovah Feldshuh) and her boss, Josh (Scott Cohen), whom she dated in college — but is it really so unreasonable to expect a man not to say "self-defecating" when he means "self-deprecating"? On a whim, Jessica answers a personal ad that includes one of her favorite quotations from Rilke, recklessly ignoring the fact that it's in the "women seeking women" section. The ad was placed by Helen (Heather Juergensen), a sexually adventurous, downtown art-gallery curator looking for a new sensation; although she's never been with a woman, she's intrigued when she gets the once-over from a lesbian at a gallery reception and, with the encouragement of her gay friends, Martin and Sebastian (Michael Mastro, Carson Elrod), figures it couldn't hurt to give the girl/girl thing a whirl. The first date is awkward — in fact, Jessica gets cold feet and tries to flee — but they wind up having plenty to talk about over drinks and dinner, and Jessica experiences a tangle of conflicting feelings when Helen impulsively plants one right on her lips. Their subsequent relationship is of the one-step-forward, two-steps-back variety: They flirt, Jessica freaks. They touch, Jessica freaks. They kiss again, Jessica freaks. "I'm a Jew from Scarsdale!" she exclaims — as much to herself as anyone else — by way of explaining her amazement that she should even be considering what she's considering. And after they finally take the plunge, Jessica is faced with a new set of problems. What should she tell her friends? How can she explain this to her parents? Why won't Helen just agree to keep their relationship a secret? Where is it all going? Co-written by stars Westfeldt and Juergensen, actresses united by their frustration with the clichéd roles available to them, the film is relentlessly peppy, often quite funny, sometimes a bit too convinced of its own adorableness and ultimately as smoothly reassuring as a TV sitcom. Imagine a lesbian-experimentation episode of Friends ("The one where Rachel goes a little bit gay") with slightly franker sex talk, and you'll be right on this ingratiating trifle's wavelength.

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  • Released: 2002
  • Rating: R
  • Review: Two heterosexual girly-girls decide to give lesbian love a try in this cuddly romantic comedy. A veteran of the dating wars, high-strung, strenuously quirky New York City copy editor Jessica Stein (Jennifer Westfeldt) is beginning to wonder whether she'll… (more)

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