Extant literature shows that small conversations with strangers can help improve individuals’ wellbeing while reducing feelings of loneliness. Nevertheless, previous studies on talking to strangers tend to focus on young participants in controlled experimental settings, leaving a gap in understanding older adults’ experiences and their likelihood of adopting talking to strangers as part of their daily healthy ageing practices. Considering the problem of worsened social isolation and loneliness among older people during the Covid-19 pandemic, it is even more important to include them in the promotion of social inclusion through micro-conversations with strangers. To understand older adults’ attitudes and experiences of talking to strangers, this study interviewed 19 older people based on their trial of talking to strangers over a three-month period. Findings reveal that their willingness and confidence varied by age and gender, with retired individuals being more active in engaging with strangers. Time constraints and lack of self-efficacy were identified as barriers, particularly among those still working or with caregiving responsibilities. Rather than personal gains, the act of kindness towards others was emphasised as the key motive. These insights are valuable for policy makers and organisations supporting older people’s wellbeing, highlighting the potential for older individuals to serve as conversation initiators, promoting mutual kindness and wellbeing in communities.