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.

Kissing Jessica Stein是2001年美國獨立的浪漫喜劇電影，由電影的明星Jennifer Westfeldt和Heather Juergensen共同創作。這部電影還由託爾斯·費爾德舒（Tovah Feldshuh）飾演，由查爾斯·赫爾曼（Charles Herman-Wurmfeld）執導。