Loneliness is well documented as a major, yet preventable, risk factor for well-being among older adults that was exacerbated by the COVID-19 pandemic. Nearly half of some countries’ older population experience loneliness, which significantly increases risks for dementia, heart disease, stroke, depression, anxiety, hospitalization, and even hastened death. Utilizing socioemotional selectivity theory, the current study addresses. the inverse relationship between aging and social outlet availability by providing empirical data on the benefits of intergenerational programming. Data from adult–college student dyads who participated in a telephone reassurance program focused on reminiscence guiding were analyzed to determine outcomes of participation. Qualitative analyses revealed the emergence of themes surrounding familial/friendship bonds and self-discovery among adult participants and a rejuvenated appreciation for the little things in life as well as a sense of purpose from meaningful contributions among college student participants. Results are discussed in terms of continued growth and development during late adulthood and professional and personal growth among students. The psychologically and emotionally meaningful nature of quality intergenerational programs provides a platform for the formation of unique relationships to offset fractured social outlets during later life, providing protections against loneliness and work to establish unique relationships between disparate groups who otherwise may never have crossed paths.