Kissing Jessica Stein (2002, Fox Searchlight), is about Jessica (Westfeldt) 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.