The WHO Commission on Social Connection reported in 2025 that one in six people worldwide experience loneliness. In this article we evaluate a design workshop which aimed to develop design concepts that addressed unwanted loneliness among older adults through a relational design perspective. The workshop also challenged ageism and ableism. Its structure was interdisciplinary, intergenerational and international. Participants applied contextual analysis and evaluated the design proposals generated by six groups. The international workshop took place in Mexico City with 18 participants. Over five days of work, participants attended lectures by aging experts, and joined roundtable discussions with older Mexicans, applied the contextual analysis tool, did fieldwork and held sessions for analysis and synthesis. Six design directions were generated through core concepts, key insights and contextual dimensions. We show how transition-oriented learning environments can cultivate the mindset and posture shifts required for long-term systems change.