Jessica (Jennifer Westfeldt) is at the end of her emotional rope. 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. She meets funky downtown hipster Helen Cooper (Heather Juergensen) for drinks, and to her surprise, they click instantly. With conventional gender roles absent, the two women proceed to muddle through an earnest but hilarious courtship, making up the rules as they go.