The role of memory in supporting adolescents' sense of place and past is not well understood, but older adults offer a wealth of life stories and wisdom that they can share with younger generations. This in-depth pilot study positioned Australian high school students as oral historians to interview older Australians about their lives. Oral historian training and materials were provided, and pre- and post-intervention measures of adolescents' sense of everyday Australian history, well-being, and social connection were collected for an intervention school group (n = 17) and a waitlist control school group (n = 12). In-depth supplementary memory and well-being data were also collected for six participating older adults. In the intervention condition, scaffolded memory interviews took place during weekly aged care visits across one school term and were followed by an intergenerational celebration and memory book presentation. As hypothesised, older adults imbued their stories with life lessons for adolescents. Although no quantitative changes in participants' well-being emerged, qualitative data revealed the emergence of rich interpersonal relationships and bonding between adolescents and older adults. There were also benefits of the programme for older adults' reports of generativity and adolescents' understanding of everyday Australian history. The findings demonstrate the social and academic benefits of scaffolded intergenerational memory conversations and represent a scalable educational model and materials with downstream community benefits.