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  1. Kissing Jessica Stein is a 2001 American independent romantic comedy film, written and co-produced by the film's stars, Jennifer Westfeldt and Heather Juergensen. The film also stars Tovah Feldshuh and is directed by Charles Herman-Wurmfeld. It is one of the earlier film appearances of actors Jon Hamm and Michael Showalter.

  2. Apr 5, 2002 · Kissing Jessica Stein: Directed by Charles Herman-Wurmfeld. With Jennifer Westfeldt, Tovah Feldshuh, Heather Juergensen, Esther Wurmfeld. A woman searching for the perfect man instead discovers the perfect woman.

  3. Mar 13, 2002 · 83% Tomatometer 121 Reviews 65% Audience Score 10,000+ Ratings Jessica (Jennifer Westfeldt) is at the end of her emotional rope. She happens upon an intriguing personal ad, whose only drawback is...

    • (121)
    • Romance, Comedy, LGBTQ+
    • R
  4. Jun 10, 2022 · Heather Juergensen and Jennifer Westfeldt open up to TODAY Show about the 2002 lesbian rom-com “Kissing Jessica Stein" in tandem with its 20th anniversary.

  5. Jessica Stein (Jennifer Westfeldt) is a 28-year-old sensitive, but neurotic, New York journalist who is at the end of her emotional rope. Her brother Dan (David Aaron Baker), is engaged. Her best friend and co-worker Joan (Jackie Hoffman) is pregnant.

  6. 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.

  7. Release date: 2002. Genre: RomanceRomantic ComedyComedy. Rating: Director: Charles Herman-Wurmfeld. Starring: Jennifer Westfeldt Heather Juergensen Scott Cohen Jackie Hoffman Michael Mastro Carson Elrod. Jessica Stein begins an intense friendship with a career woman...which ultimately leads to romance.

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