The introduction first examines the evolving meaning(s) of the term “cringe” in the twenty-first century before addressing the paradox of cringe humor, which derives amusement from embarrassment. Three hypotheses are proposed to explain the interplay of these emotions: (1) amusement arises after embarrassment, aligning with release theories of humor; (2) amusement and embarrassment occur simultaneously, in keeping with McGraw and Warren’s Benign Violation Theory; (3) embarrassment and mirth arise in alternation, stemming from distinct cringeworthy and humorous stimuli. The introduction then differentiates cringe humor from other types of controversial humor and establishes an etic, second-order definition of cringe humor as a form of affiliative humor, designed to elicit amusement through embarrassment. We argue that this effect is achieved by showcasing its reception as ambivalently cringeworthy and amusing thanks to ‘indicators of reflexivity,’ of which we provide a non-exhaustive list. Finally, we account for the emergence of cringe humor in the twenty-first century, suggesting that this type of humor negotiates the tension between the desire to offend and the ethical responsibility to avoid offending protected groups in a “post-politically correct” world, hence its emphasis on embarrassment. The introduction concludes by justifying the pragmatic approaches to cringe humor adopted in the book to make sense of the spectrum of reactions it elicits—from appreciation to rejection—and to interrogate its outer boundaries.