Young Sam Callahan (Bug Hall) is reaching an age where his curiosity about the opposite sex and his possible interactions with it is reaching a boiling point. As an aspiring writer, he needs this information to give his stories realism. With the help of his mother (Jennifer Jason Leigh) and equally interested classmate Maurey (Mischa Barton), Sam begins his coming of age with a voyage of discovery into the world of sex. Soon, he leaves behind his image of a perfect woman (Drew Barrymore) to find himself romantically entangled with fellow voyager Maurey.