Changes in traditional family structures, public policy arrangements, and new family care patterns are reducing opportunities for interaction between younger and older people in Europe and in Italy, especially when the latter live in residential care facilities. This may bolster age-related stereotypes in both generations and end up with affecting older people's self-confidence, devaluing their emotional and relational capabilities. “ Let's Re-Generate” is a pilot research-action project—based on an intergenerational program carried out in a nursing home in Central Italy—which aimed at prompting institutionalized older people and adolescents in the community to enhance intergenerational ties through various shared activities. Results from focus groups with 25 teenagers and in-depth interviews with 16 older residents and 16 older volunteers provide an in-depth insight on the positive impact of intergenerational programs, which foster the interaction between different ages, help overcome age-related stereotypes, and improve older people's mental well-being and older volunteers' generativity. The main recommendation emerging from this study is that intergenerational activities should be integrated in the daily routine of nursing homes, acting as useful tools for fostering older residents' capability of reacting to dependency and social isolation.