Vulnerability is the feeling of being exposed and unable to withstand the effects of a hostile environment—something we typically wish to avoid. This paper aims to develop and propose vulnerability as an asset when designing for interpersonal interactions. Initiatives investigating how design can foster social resilience, developed for the Central Saint Martins, University of the Arts London Cultures of Resilience project, serve a reference to analyze how designers can address interpersonal vulnerability in design practices. I identify various enablers of vulnerability for each initiative and analyze them in relation to the theoretical framework I propose. The main benefit of designing for vulnerability that it enables the possible emergence of I-You relations between participants. The I-You relations are considered one of a human being’s most distinctive features.