Second couplehood in old age is a growing phenomenon alongside increases in life expectancy. Lately, a shift has occurred in that individual diversity of ageing is perceived to depend on the physical and social contexts in which older persons experience change. Thus, the purpose of the study on which this paper reports was to examine second couplehood in the context of old age and old age in the context of second couplehood using an existential-phenomenological theoretical orientation. Twenty couples were recruited using criterion-sampling: men aged 65+ and women aged 60+, with children and grandchildren from a lifelong marriage that had ended in widowhood or divorce, living in second couplehood – married or not – in separate houses or co-habitating. Forty individual semi-structured interviews were tape-recorded, transcribed verbatim and analysed according to phenomenological tradition. Five sub-themes emerged, demonstrating couplehood and old age intertwining: (a) enjoying life while still possible; (b) living with health-related issues; (c) relationships with adult children: autonomy versus dependency; (d) loneliness: living as a couple is better than living alone; (e) self-image: feeling young–feeling old. Findings support the existence of positive and negative aspects of old age. Our discussion suggests the need to replace perceptions of old age as either a negative burden or a positive asset towards a period of balancing between gains and losses. Furthermore, we acknowledge the role of second couplehood in older peoples’ wellbeing on the personal–micro level through love, the familial–mezzo level through care-giving and the social–macro level by reducing prejudice.