The beautiful Aileen Hingston and her dashing beau Shirley Davidson set off on a gentle Sunday morning sail in August 1907. Despite being excellent sailors and swimmers, the couple failed to return to the Hingston summer home at Varennes, a small town just south-east of Montreal, where they were expected for lunch. The sudden, mysterious disappearance of these two young Montreal celebrities captivated the public imagination. While people speculated and gossiped about whether this was a suicide pact, a tragic accident, or a staged escape, the family and friends of Aileen and Shirley were caught in the horror of searching the riverbanks and depths of the St. Lawrence for any sign of their loved ones. For five days, the search for the two young people was relentless and when the end arrived, it was the most tragic denouement. This is a story that is dramatic and harrowing, played out across an urban and rural landscape that was rife with palpable tensions emerging where language, religion, gender, and class clashed. The sensationalism of this tragedy, driven by the youthfulness and celebrity status of the central actors, magnified the way narratives competed: one narrative driven by spectacle and speculation, the other driven by devotion and a desire for respectability. When we unpack this story, paying attention not only to the events themselves but also to the conversations that were happening in the public and private spaces of Montreal, we glean invaluable understandings of the ways these tensions were experienced and, in some instances, mitigated. We see, for example, that capital, both social and material, could provide a buffer from certain types of public disgrace, while private moral judgements were harder to combat and often lingered in the whispered realm of gossip, only emerging in written form once time and space had created enough distance from the trauma.