Kissing Jessica Stein (2002)
Jessica, a Jewish copy editor living and working in New York City, is plagued by failed blind dates with men, and decides to answer a newspaper's personal advertisement. The advertisement has been placed by 'lesbian-curious' Helen Cooper, a thirtysomething art gallerist.
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Cast
- Jennifer Westfeldt — Jessica Stein
- Heather Juergensen — Helen Cooper
- Scott Cohen — Josh Myers
- Jackie Hoffman — Joan
- Tovah Feldshuh — Judy Stein
- Michael Mastro — Martin
- Carson Elrod — Sebastian
- Jon Hamm — Charles
- David Aaron Baker — Dan Stein
- Esther Wurmfeld — Grandma Esther
- Hillel Friedman — Rabbi
- Ben Feldman — Ben Feldman
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