Kissing Jessica Stein (R, 2001)

Jessica is the highly neurotic and previously straight (and sexually repressed) half, of a lesbian couple struggling to find intimacy, love, and personal satisfaction. Living in present-day New York, Jessica (Jennifer Westfeldt) and Helen (Heather Juergensen) struggle with bad dating, old and current boyfriends, a crazy Jewish mother, and confusing feelings. Jessica does not know what she wants. Her mother just wants her to settle down with a nice Jewish man, while Helen wants to find the perfect combination of love and sexual heat. Ultimately, the couple must investigate their own feelings about love, sex, and friendship and go for broke in their searches for personal fulfillment.

KISSING JESSICA STEIN is a witty and hysterical romp through sexual discovery. It transcends the label of "lesbian comedy" to succeed as a romantic comedy that illustrates the feelings and struggles common to all. Aside from strong performances by its lead women, the film also includes inspired performances by Jackie Hoffman as Jessica's wacky coworker/best friend and Tovah Feldshuh (Law and Order and Broadway) as her domineering mother. As an added bonus, the film also includes a hysterical and odd performance by JM J Bullock (Too Close for Comfort [1980] and The Jim J. and Tammy Faye Show [1996]) as one of Jessica's bad dates.