Kissing Jessica Stein (2002)

When it comes to love, sometimes she just can't think straight.

Movie · Comedy · 1h 37m · Rated 6.0/10 on TMDB · Released March 13, 2002

Overview

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.

Directed by Charles Herman-Wurmfeld

Cast

• Jennifer Westfeldt as Jessica Stein
• Heather Juergensen as Helen Cooper
• Scott Cohen as Josh Myers
• Jackie Hoffman as Joan
• Tovah Feldshuh as Judy Stein
• Michael Mastro as Martin
• Carson Elrod as Sebastian
• Jon Hamm as Charles
• David Aaron Baker as Dan Stein
• Esther Wurmfeld as Grandma Esther
• Hillel Friedman as Rabbi
• Ben Feldman as Ben Feldman

More like this

• Die, Mommie, Die! (2003)
• Driver's Ed (2026)
• Hard to Die (1990)
• Ali Wong: Single Lady (2024)
• The Wedding Year (2019)
• Adam Sandler: Love You (2024)
• Bill Burr: Drop Dead Years (2025)
• Desperately Seeking Susan (1985)
• Ladies First (2026)
• A Night at the Opera (1935)
• Like a Boss (2020)
• Chris D'Elia: Man on Fire (2017)

Movie and show details come from TMDB. This product uses the TMDB API but is not endorsed or certified by TMDB.