During her sophomore year at Middlebury College, Emily meets Max – 'you' as she intimately refers to him in the book.

Not exactly a tomboy, but not quite a girly girl either, Emily is intent on finding a masculine boyfriend to assuage a deeply rooted fear that she may not be quite feminine enough. Max, who loves Maria Von Trapp and shot-gunning beers with his straight guy friends, is grieving his first great heartbreak, to a boy on the new season of MTV's The Real World.

Initially, Max and Emily dislike each other, but end up growing close after a make-out dare on Halloween. Then one night, Max reveals an unexpected physical attraction that catches them both by surprise. The experiment begins, in secret, and then spirals into something more. Emily fears the unknown in a relationship with someone who doesn't fit her traditional idea of a masculine partner. And although Max deeply loves Emily, he cannot change the fact that he is attracted to men.

Max and Emily's journey takes many forms – they experiment with drugs; they travel abroad; they try sleeping with other people (together), and everything in between – all in the name of 'this bizarre, beautiful thing' they call love.