Kissing Jessica Stein (2001) - Synopsis
Kissing Jessica Stein (2001) is a laugh-out-loud comedy with a fresh take on sex and the single girl. When we first meet Jessica - a sensitive but neurotic New York journalist - she is at the end of her emotional rope. Her brother's engaged, her best friend's pregnant, her mother’s on her case, she hasn't had a decent date in a year, and if that weren’t enough…she’s got insomnia.
After a dating spree from hell, 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 answers it and meets funky downtown hipster Helen Cooper. To Jessica’s surprise, they click instantly. Their evening of banter and heated debate culminates in a kiss that confounds and intrigues even the reluctant Jessica.With conventional gender roles absent, the two women proceed to muddle through an earnest, but hilarious courtship, making up the rules as they go along.