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During the COVID-19 pandemic, risk negotiation became an important precursor to in-person contact. For young adults, social planning generally occurs through computer-mediated communication. Given the importance of social connectedness for mental health and academic engagement, we sought to understand how young adults plan in-person meetups over computer-mediated communication in the context of the pandemic. We present a qualitative study that explores young adults’ risk negotiation during the COVID-19 pandemic, a period of conflicting public health guidance. Inspired by cultural probe studies, we invited participants to express their preferred precautions for one week as they planned in-person meetups. We interviewed and surveyed participants about their experiences. Through qualitative analysis, we identify strategies for risk negotiation, social complexities that impede risk negotiation, and emotional consequences of risk negotiation. Our findings have implications for AI-mediated support for risk negotiation and assertive communication more generally. We explore tensions between risks and potential benefits of such systems.