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Kissing Jessica Stein Trailer

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Published on Aug 23, 2016

Jessica (Jennifer Westfeldt) is at the end of her emotional rope. She happens upon an intriguing personal ad, whose only drawback is that it's in the "women seeking women" section. On a daring whim, she decides to answer it. She meets funky downtown hipster Helen Cooper (Heather Juergensen) for drinks, and to her surprise, they click instantly. With conventional gender roles absent, the two women proceed to muddle through an earnest but hilarious courtship, making up the rules as they go.

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 also one of the first film appearances of actor Jon Hamm. The film is based on a scene from the 1997 off-Broadway play by Westfeldt and Juergensen called Lipschtick.

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