This article focuses on the structures of humor and joke telling that require particular kinds of attentiveness and particular relationships between speaker and audience, or more specifically, between classmates. First, I will analyze the pedagogical and relational preconditions that are necessary for humor to work. If humor is to work well, the person engaging in humor needs to gauge their interlocutors carefully. I discuss, too, the kinds of listening necessary for listening for the joke, including attentiveness to complex possibilities for meaning. This attentiveness to complexity is linked to curiosity and a willingness to be startled, two qualities that are central to the risk and pleasure of learning discussed by Socrates and Maria Lugones. Examining the place of risk in Socrates' teaching and the place of serious play in Maria Lugones' discussion of difference, I suggest that humor can help to illuminate complicities and invite more robust interactions with difference, creating pleasurable encounters to work through difficult social divisions.