Existing research surrounding dating apps has primarily focused on younger people with few studies exploring usage of such apps by middle aged and older adults. The worldwide COVID-19 pandemic challenged social behaviours and forced people to adapt intimacy and wider relationship conduct. The objective of this study was to examine how older adults utilized dating apps during the lockdowns of the UK pandemic (December 2020–May 2021). Findings presented here focus on qualitative data collected from an online survey and eight online, one-to-one interviews with adults aged 40–54 years. The online survey targeted adults across the UK while interviewees were located across England. Employing interpretative phenomenological analysis, findings identified three key themes: 1. Morality, health, and law breaking and COVID-19; 2. Self-surveillance and moral signalling; 3. Loneliness and social isolation. Qualitative findings show engaging with apps was a proxy which alleviated feelings of loneliness and social isolation. Some users used the premise of their social bubble as a way of meeting other people. Using the same premise, others justified breaking the law to engage in physical and sexual intimacy to mitigate their loneliness. The work presented here contributes to the fields of social sciences, gerontology, and human computer interaction. The inter- and multi-disciplinary impact of this study intersects across those fields and offers a cross-sectional insight into behaviours and engagement with technology during one of the most extraordinary global events.