Kissing Jessica Stein
Directed by Charles Herman-Wurmfeld
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- Edgardo LopezFebruary 7, 2026I remember reading about this long ago and I never got around to watching it until now. It reminded me a little bit of Chasing Amy but obviously the romance role was reversed. I thought it was a cute and funny movie and it had moments that hit in the feels. Their dynamic felt genuine and they had good chemistry, unfortunately I was able to see the ending coming and was not surprised. The ending felt a bit rushed and didn’t feel complete. The movie spends the majority of its runtime building up to a happy arch in the story and then a quick ending that made me feel that the editing team gave up or production ran out of money or something. Overall, it’s a good movie, and falls into that category of alternative romance comedy.
- dial14August 17, 2025I love this movie! Kissing Jessica Stein is Woody Allen-esque romcom about an obsessive and overly-judgmental intellectual who can't get out of her own way, and who, in desperation, turns to a surprise connection with another woman, and has to learn how to navigate a same-sex relationship that she is in no way prepared for. It's an inspired comedy, with fully realized characters who fence with witty dialogue which, while sharp and funny on the surface, has layers beneath. The banter is delightful, funny and real, and comes embedded in situations that keeps you smiling and cringing between punchlines. The characters are so specific and believable, that even staples of the form, like the fear of ending up alone, feel compelling and deeply recognizable. I laughed, I cried, felt seen, I was comforted. Top marks!
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Kissing Jessica Stein Trivia
Kissing Jessica Stein was released on December 7, 2001.
Kissing Jessica Stein was directed by Charles Herman-Wurmfeld.
Kissing Jessica Stein has a runtime of 1h 37m.
Kissing Jessica Stein was produced by Brad Zions, Eden Wurmfeld.
Jessica Stein is a single, straight, successful, journalist, part of a bonded Jewish family living in New York City, who finds herself not as straight as she thought when Jessica meets and begins an intense friendship with career woman Helen Cooper which ultimately leads to romance.
The key characters in Kissing Jessica Stein are Jessica Stein (Jennifer Westfeldt), Helen Cooper (Heather Juergensen), Josh Myers (Scott Cohen).
Kissing Jessica Stein is rated R.
Kissing Jessica Stein is a Comedy, Drama, Romance film.
Kissing Jessica Stein has an audience rating of 6.5 out of 10.
Kissing Jessica Stein had a budget of $1M.
Kissing Jessica Stein has made $10M at the box office.