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  1. Jun 10, 2022 · They didn’t know it right away, but when Heather Juergensen and Jennifer Westfeldt met at a New York theater retreat in the late ‘90s, it was kismet.

    • Scott Cohen Got Arrested
    • Jennifer Westfeldt Was Tovah Feldshuh’S Assistant
    • Charles Herman-Wurmfeld Fought to Direct
    • Michael Showalter Improvised All His Lines
    • Jon Hamm Was Supposed to Play Josh
    • Audiences Hated The Original Ending, So They Changed It
    • A Lasting LGBTQ Legacy

    Kissing Jessica Steinwas a small production, and often shot in friends’ and families’ homes. When filming at Westfeldt’s parents’ house in Connecticut, Scott Cohen (who played Jessica’s prickly boss Josh) was mistakenly arrested while getting coffee at a nearby deli. “I hear this siren behind me. This cop gets out of his car, and he puts my hands b...

    One of the best scenes in Kissing Jessica Stein is the conversation between Jessica and her mother, Judy (Tovah Feldshuh), on their front porch, when Judy acknowledges Jessica’s relationship with Helen. While the chemistry came from the writing, it was enhanced by the time that Westfeldt worked as Feldshuh’s assistant. During that gig, Feldshuh rem...

    When looking for a director, initially Juergensen and Westfeldt wanted someone with more experience, since they themselves were so green in the movie-making process. Westfeldt had called up Eden Wurmfeld, a friend of hers, who was a pretty experienced indie film producer and, as Westfeldt describes, the “adult” of the group. Wurmfeld’s brother, Cha...

    There’s a lot of random celeb spotting when watching Kissing Jessica Steintoday — stars like Idina Menzel and Michael Ealy show up. And comedian/actor/director Michael Showalter appears as one of Helen’s many lovers in an early scene. It’s something that wouldn’t be terribly memorable if Showalter didn’t talk about hanging a bookmark off his genita...

    While Scott Cohen ended up playing the role of Josh, as recommended by Camryn Manheim, Jon Hamm originally read for the part with Juergensen and Westfeldt. If you are a Kissing Jessica Steinsuperfan, you’ll know he has a small role as a guy Jessica’s friends try to set her up with in the beginning of the film. Juergensen said that when it came time...

    While some audiences still were disappointed with the Kissing Jessica Stein ending (Westfeldt jokes about always having divisive endings in her films) the original reallypissed people off. Juergensen says the ending they originally shot had Jessica go to Josh’s house with clear intentions of seeing him, instead of them running into one another. “Th...

    The film earned critical acclaim at release but also garnered criticism for its ending (Jessica and Helen — spoiler alert! — don’t end up together). Yet it still resonates with the LGBTQ community. Jackie Hoffman (Feud), who played Jessica’s pregnant BFF, remains proud of the film. “Lesbians, first of all, love it. One time it was a cop who says, ‘...

  2. Jun 17, 2022 · As working actors, Heather Juergensen and Jennifer Westfeldt met at a theater retreat and had the spark of the idea that would eventually become Kissing Jessica Stein.

  3. Then came what Westfeldt and Juergensen called the worst part of making “Kissing Jessica Stein.” It was “getting the money,” Westfeldt said, to which Juergensen added that the effort was “absolutely, positively the hardest, the worst.

  4. 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 .

  5. Apr 5, 2002 · That's just what copy editor and hopeful painter "Jessica" (Jennifer Westfeldt) does in "Kissing Jessica Stein" leading to an awkward first encounter, then a close friendship and ultimately an intimate relationship with a stunning, smart and funny art gallery manager, "Helen" (Heather Jurgenson).

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  7. Mar 10, 2002 · Now a critic at Variety was saying ''Kissing Jessica Stein'' was ''pure pleasure,'' and praising the ''pitch-perfect performances with deliciously smart writing by Jennifer Westfeldt and...