This comparative study of Tristan Bernays’ Old Fools (2018) and Nick Payne’s Elegy (2016) concerns two contemporary plays in which love manifested in middle-age and older adulthood is a determinant factor in the reconceptualization of the ageing self, particularly when afflicted by memory loss or cognitive failure. Positioned within the framework of theatre and ageing studies, and drawing from their intersection with gender studies and disability theories, the study demonstrates that the narrative arc that both texts recreate is not free of overtones of decline. However, the manipulation of chronological time in both plays through different techniques, as well as the importance of their love story, one between a man and a woman in Old Fools, and the other between two women in Elegy, help disrupt the binary of young/old perpetuated by ageist cultures, and, ultimately, undermine rigid constructions of identity in old age. The article concludes that new theatrical representations of ageing that develop narratives of love not only enable richer debates on the construction of the self, but ultimately contribute to an all-inclusive stage and, with it, to an age-friendly society.