The majority of instructional communication literature has historically focused on the positive outcomes of incorporating humor into the classroom. However, despite the clearly documented instructional benefits of humorous communication, the literature tends to focus solely on instructor-enacted humor. However, humor is not a homogenous concept; therefore, it is imperative to examine it from a number of contexts, including student-enacted humor. Although the Instructional Humor Processing Theory (IHPT) has made a number of theoretical advances in exploring humorous communication in the classroom, it still lacks adequate explanatory power, particularly when examining student-enacted humor. Thus, four expansions to IHPT are proposed: to incorporate (a) the interpersonal attraction experienced toward the sender, (b) the humor orientation of the receiver, (c) the enacted humor style of the sender, and (d) the receiver’s perception of the classroom climate. Results indicate that the aforementioned expansions are theoretically pertinent to examining student-student humorous communication and warrant future research for inclusion to IHPT. The study also discovered sex differences regarding the message sender, along with interaction effects between the sex of the sender and receiver. Theoretical and practical implications of these results are discussed, and directions for future research are provided.