Loneliness is a prevalent phenomenon within the older adult population. Previous literature suggests that technology use, specifically internet use, can alleviate loneliness and improve wellbeing. This research study follows 32 people over the age of 65 using a digital technology for six months. A mixed-method approach was used to collect quantitative and qualitative data throughout the time period. The repeated questionnaire measured changes in frequency of use, emotional attachment towards a device, a sense of belonging and perceptions of self-worth, whilst an event-based diary was used to note usages and influences of technology on lifestyle. Results revealed positive relationships between frequency of use and emotional attachment and frequency of use and perceptions of self-worth. There was no significant relationship between frequency of use and a sense of belonging for the aggregate data. There was, however, a negative relationship between emotional attachment towards a device and a sense of belonging, suggesting a fine balance between technology use to improve self-esteem through connections with social networks and an over-dependence on technology that can actually reduce feelings of belonging.