Kissing Jessica Stein (2002)

After an optimistic but nightmarish dating spree, neurotic New York journalist Jessica Stein 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, to her surprise, ends up instantly clicking with downtown hipster Helen Cooper. The women proceed to muddle through an earnest courtship in which, with conventional gender roles absent, they are forced to make it up as they go along.