People are increasingly acquiring huge collections of digital possessions. Despite some pleas for ‘forgetting’, most theorists argue for retaining all these possessions to enhance ‘total recall’ of our everyday lives. However, there has been little exploration of the negative role of digital possessions when people want to forget aspects of their lives. We report on interviews with 24 people about their possessions after a romantic breakup. We found that digital possessions were often evocative and upsetting in this context, leading to distinct disposal strategies with different outcomes. We advance theory by finding strong evidence for the value of intentional forgetting and provide new data about complex practices associated with the disposal of digital possessions. Our findings led to a number of design implications to help people better manage this process, including automatic harvesting of digital possessions, tools for self-control, artifact crafting as sense-making, and digital spaces for shared possessions.