Emerging personal lifelog (PL) collections contain permanent digital records of information associated with individuals’ daily lives. This can include materials such as emails received and sent, web content and other documents with which they have interacted, photographs, videos and music experienced passively or created, logs of phone calls and text messages, and also personal and contextual data such as location (e.g. via GPS sensors), persons and objects present (e.g. via Bluetooth) and physiological state (e.g. via biometric sensors). PLs can be collected by individuals over very extended periods, potentially running to many years. Such archives have many potential applications including helping individuals recover partial forgotten information, sharing experiences with friends or family, telling the story of one’s life, clinical applications for the memory impaired, and fundamental psychological investigations of memory. The Centre for Digital Video Processing (CDVP) at Dublin City University is currently engaged in the collection and exploration of applications of large PLs. We are collecting rich archives of daily life including textual and visual materials, and contextual context data. An important part of this work is to consider how the effectiveness of our ideas can be measured in terms of metrics and experimental design. While these studies have considerable similarity with traditional evaluation activities in areas such as information retrieval and summarization, the characteristics of PLs mean that new challenges and questions emerge. We are currently exploring the issues through a series of pilot studies and questionnaires. Our initial results indicate that there are many research questions to be explored and that the relationships between personal memory, context and content for these tasks is complex and fascinating.