If “humor goes awry in the classroom” were a headline, we could all immediately imagine multiple scenarios based our own experiences or stories we’ve heard. Perhaps a student takes a teacher’s joke literally (e.g., a teacher saying “I want you to laminate these paper guidelines because you’ll be using them so much in all your classes” results in a student laminating the assignment handout). A more difficult situation might arise when a teacher teases a student in a friendly manner, but the student misinterprets the teasing and takes the teacher’s comments personally.
We do things because they work for us in some way. For example, I need students to be talking and writing and sharing a lot in my workshop classes for those classes to be successful. I sometimes use humor with them to help loosen them up. Ideally, they will share more comfortably and be less worried about saying “the right thing,” and realize they need to just start saying things and revising those things. Over the years, I have discovered that sometimes students may be intimidated by my use of technical vocabulary or by my sheer verbosity. I am an English teacher after all. I have learned that teasing students in the context of workshops can often go awry for me. They think I’m making fun of them because they don’t think I might feel the same frustrations they do. I’m the expert, so I must be making fun of their lack of expertise. One technique I use quite often is to tell stories making fun of my own messy invention work and my own frustrations with writing.
In general, I would say the more technical your lesson or class and the more your students are struggling to understand your explanations, the more careful you should be about teasing students individually. I’d also steer clear of indirect teasing or complimenting if your students are stressed out. In order to avoid confrontation about cell phone use during workshops, for example, it would probably be a mistake to joke with an offending student that he should put his phone away so that he could help this other student who is having so much trouble with his homework. The second student in this case might realize that he’s obviously high achieving so the teacher is obviously joking, or he may feel he is being unfairly criticized on his homework quality.