Kissing Jessica Stein (2001)

Jessica Stein is a sensitive but neurotic New York journalist who also happens to be at the end of her emotional rope. Her brother's engaged, her best friend's pregnant, she hasn't dated in a year, and she can't sleep. After an optimistic but nightmarish dating spree, she happens upon an intriguing personal ad, whose only drawback is that it's in the "women seeking women" section. On a daring whim, she decides to answer it, and meets funky downtown hipster Helen Cooper. A lively evening of banter, connection and heated debate culminates in a kiss that confounds and intrigues even the reluctant Jessica. Kissing Jessica Stein is a modern romantic comedy that breaks all the rules, blurring the lines between friendship and romantic love, and finding the funny, surprising and ultimately poignant overlap between the two.