Kissing Jessica Stein

New York City remains a busy backdrop as Jessica Stein, a Jewish copy editor, reels from endless failed blind dates and a sense that love is elusive. She answers a newspaper personal ad placed by Helen Cooper, a thirtysomething art gallery owner who hints at being curious about women. The initial encounter feels playful and unexpected, and the two women begin spending time together outside their usual routines. What starts as a flirtation grows into a deeper exploration of attraction, identity, and what romance can mean for a person who has always followed a certain script. As they test boundaries and question assumptions, the friendship quietly reshapes Jessica's ideas about love, commitment, and taking chances.

Directed by Charles Herman-Wurmfeld, the film stems from the collaboration of Jennifer Westfeldt and Heather Juergensen who wrote an original screenplay inspired by their own experiences and conversations about dating, desire, and the spectrum of attraction.

Box office wise it grossed 10,013,424 dollars worldwide on a budget of 1,000,000 dollars, showing strong indie performance for a character driven romantic comedy and helping establish the film as a indie hit that found a dedicated audience over time.

As one of the earlier mainstream films to center a lesbian tinged romantic plot in a broad release, it sparked conversation about representation and dating across sexual lines rather than leaning on stereotype or punchlines. Its accessible tone and humor helped broaden conversations about same sex romance.

Critics noted the sharp dialogue, warm performances, and frank handling of desire and identity. The film blends urban dating humor with themes of self acceptance, female friendship, and the courage to redefine what love can look like. Its warmth invites viewers to rethink how love is defined in modern life.