Ashton Clarke, a local Casanova with a long history of falling into bed with a different woman every night, is perfectly content with her free and easy existence, until she gives in to her best friend's request to spend an evening helping out at the local gay and lesbian youth center. There, Ash meets Carrie Fletcher, a women's studies professor who not only intrigues Ash but causes her to question the direction her life has taken.

As if this disquieting attraction isn't aggravating enough, Ash is forced to deal with Carrie's teenage neighbor, Tess, whose bad attitude and biting wit seem to complicate every situation. Ash doesn't want to be attracted to Carrie, who isn't looking for a relationship with anyone, and Tess is angry at the world, but especially, it seems, with Ash. Despite resistance on the part of all three women, it soon becomes obvious that the trio's destinies are hopelessly intertwined, and the lessons in store will change all their lives.