The Positive Pen Pal Program is an intergenerational initiative designed to increase the well-being of senior and youth residents at Education Based Housing, Inc.’s (EBH) affordable housing communities through communication exchanges involving writing about positive events and experiences, art, and music. The pilot program involves a month-long, bi-directional letter writing exchange about topics such as gratitude, meaning, and purpose between ten pairs of residents, with each pair comprised of a senior resident and a youth resident. This project provides a stand-alone playbook for EBH’s Resident Engagement Specialists. The playbook includes a brief introduction to well-being; sample recruitment letters for seniors and youth; sample instruction letters for seniors and youth; sample prompts for writing about positive events and experiences, art, and music; sample marketing information to solicit sponsorship from community businesses; measurement tools to assess aspects of well-being of the participants; and survey questions to assess the impact of the program on the participants. The implications of this work include enhanced understanding of the interplay among positive psychology, the humanities, and intergenerational interventions in affordable housing communities. Beneficially, this intervention is low-resource and expandable across multiple humanities domains and residential communities.