Abundant HCI research exists on the many assistive technologies that provide help with everyday physical and cognitive tasks. However, while a purely assistive approach often casts aging people in passive roles, recent studies suggest that adults may be ‘flourishing’ way into advanced age, even though implicit ageist prejudices are difficult to eradicate. Negative age-related stereotypes are the hidden and yet urgent issue we address in this study. There is a clear opportunity for an anti-ageist perspective in HCI, an approach that we propose as complementary to assistive technologies: in addition to providing solutions for the aging population, we urgently call for designs about aging, to spark a conversation on age, raise awareness and ultimately contrast ageist stereotypes. We point at empathy as a key element to reconceptualize, at least in part, HCI’s contribution to research on aging. We present a design critique of two interactive pieces that, although not without flaws, suggest how future empathy-raising artifacts might be. Our analysis combines pragmatist aesthetics, interaction criticism and ludology, and yields four design tactics (recurring configurations of significant elements) that are generative in bringing about broader design implications towards a different, empathy-based concept of aging in HCI.