This chapter focuses on cringe humor in the British TV series Fleabag (BBC Three, 2016–2019) and largely builds on the theoretical framework of humor defined by McGraw et al. (2014) and Warren and McGraw (2016) and on prior discussions of Fleabag. It provides a comprehensive account of the mechanisms underlying the production of cringe humor in Fleabag: (not so) benign violations and their interaction with viewer knowledge, the modulation of psychological distance, and character complexity. It then accounts for the progressive fading of cringe humor between the first and the second season of the series. I argue that through direct address and gazes at the camera, the viewers are encouraged to laugh with Fleabag at other characters and to share the pleasure she takes in cringe situations. However, as the series unfolds, the viewers’ empathetic engagement with characters other than Fleabag increases, because some initially flat or ambivalent characters progressively complexify. Additionally, the viewers also gradually realize that their privileged relationship with the protagonist is actually a ploy that aims at hiding her true feelings and experience. Maintaining a balance between making the viewers cringe and making them laugh is difficult, and cringe humor appears to be a smokescreen that conceals tragic violations and that allows Fleabag to avoid what is too taboo or too emotional. This ultimately allows the viewers to feel more empathy—and perhaps compassion—toward Fleabag, so much so that empathy progressively replaces cringe humor.