Clarke has been gay since birth, and he's known it since the seventh grade. He's gone through numerous boyfriends, from the middle school-y, sweaty palms, giggling on the swing set type, to the awkwardly-holding-hands-in-the-cafeteria-because-of-a-dare type, to the I-actually-really-like-you-for-real type, but in the end, none of them work out. In a fit of desperation to help his poor, hopeless romantic of a friend, Daniel suggests that Clarke try dating a girl for the first time, to see if he "decides he likes girls more." Thus begins the bet. The rules are simple: Clarke has to find a girl that he finds relatively attractive and nice, and go on a couple of dates with her. Daniel has to do the same. But between Ye Olde Elementary School, The Last Days of Humpty The Dog, and a whole bunch of mixed-up everything, this deal is going to be a lot more confusing than anyone expected.