Research has shown that students perceive their success, in even the most difficult courses, on their interactions and relationships with their instructors (Anderson, 2011; Micari & Pazos, 2012). In the online classroom, instructors run into an even greater challenge when it comes to engaging students, showing their personalities, and being present. One way of making connections with online college students is through humor. Hackathorn, Garczynski, Blankmeyer, Tennial, and Solomon (2011) found that students not only expressed favorable comments about their professors who used humor in the classroom, they also showed higher success rates and levels of engagement. Davies (2015) also discovered that student comprehension of material delivered with wit was increased over students whose instructors did not use humor. This article will provide research behind using humor, examples of appropriate and effective means of demonstrating humor in the online classroom, and samples of student comments when humor was used. Even the most humor-challenged faculty members will learn strategies to add elements of their own wittiness to their online classes.