In the summer of 2015, the “cheating website” known as Ashley Madison came under scrutiny, as a group calling itself the Impact Team revealed users’ private information. This case study explores the controversy’s Canadian media coverage and sheds light on the main discourses about intimacy and the Internet that were made visible during this event. It interrogates how cheaters, hackers, and the company were represented. To varying degrees, the mainstream press condemns the cheaters, the hackers, and the company for their behaviour. The article also addresses the ways intimate practices are politicized and commercialized in the digital context, including a discussion of the emphasis on “privacy.” To conclude the article, I discuss the transparency and privacy issues implicated in digital intimacies and the power–knowledge (im)balance implied by hackers’ online anonymity.