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Kissing Jessica Stein (2001) Poster

Trivia

Many "extras" in the film were people who just happened to be walking by the cameras during filming in New York City.
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Some background shots were removed from the film prior to its release because they showed the World Trade Center.
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The cab scene where Helen and Jessica talk about blending lipstick was filmed after the filmmakers hailed a cab, paid the driver $20, the director drove, the director of photography was in the front seat and the sound woman climbed in the back trunk.
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The role of the mother was written especially for Tovah Feldshuh.
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The film is based on a play called "Lipschtick", the original title of the film was "Seeking Same."
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Future Broadway and Disney megastar Idina Menzel (RENT, Wicked, Frozen) has a small role in this movie.
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Kevin Sussman, who went on to play Stu, the Comic Store Owner in Big Bang Theory, has a small role in this film.
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Small screen '80s celebrity Jim J. Bullock, from Too Close For Comfort and Hollywood Squares, has a small role in this film.
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Most of the film was shot in New York City and Connecticut but a couple of scenes, including the bookstore scene between Josh and Jessica, were re-shot in Los Angeles.
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Spoilers 

The trivia item below may give away important plot points.

In the beginning of the film, Jessica is set up on a blind date by a co-worker and friend. The date was played by Jon Hamm, with whom Jennifer Westfeldt was in a real life relationship with at the time.
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See also

Goofs | Crazy Credits | Quotes | Alternate Versions | Connections | Soundtracks

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