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This article is not a research paper in the conventional sense. Instead, it is a reflexive account of the building of a relationship which would not have happened without the existence of digital technologies and might not have happened but for the impact of the Covid-19 pandemic. It was through reading a digitised resource (an online PhD thesis) in the first UK 'lockdown' that Bob, now a semi-retired academic in the field of adult and organisational learning, began to reappraise his upbringing in a children's home in Scotland. Meanwhile, it was in getting to know Bob (through emails and Zoom meetings) and by accessing Bob's retrospectively digitised case record that Viv, the author of the PhD thesis and now a semi-retired social work academic, was stimulated to revisit her early research from a fresh perspective. We argue that our real-life example, serendipitous and unique as it undoubtedly is, demonstrates the democratising potential of the digital transformation that is currently being played out in child and family social work. Furthermore, it seems likely that digital technologies will continue to bring new and unexpected opportunities for forming such relationships in the future. Plain Language Summary: In this article, two older academics (one from social work and the other from management learning) introduce their meeting online during the Covid-19 pandemic and the relationship they have been building since then, from the very different perspectives of a social work researcher and a former resident of a children's home in Edinburgh in the 1940s and 50s. Bob and Viv describe coming together as an opportunity for shared learning, and they suggest that child and family social workers should be ready for, and welcome, such opportunities. [ABSTRACT FROM AUTHOR]