The wellbeing of sexual and gender minorities (SGM) is undermined by widespread homophobia that extends to health systems, and is exacerbated by medical curricula under-representing the health needs of this key population group. In 2012, under the auspices of the Department of Obstetrics and Gynaecology at the University of Cape Town in South Africa, a student-inspired curriculum intervention led to the introduction of interactive participatory workshops centred on the health needs of SGM. This paper describes the experiences of two of the workshop facilitators who embraced the risk of introducing an unchartered topic in a student-centred manner, which frequently led to unpredictable events that were challenging. Here, the authors reflect on their own vulnerabilities, which are considered alongside the value of moving through risk to transform present curricular practices and student attitudes, especially in a country like South Africa where prejudice against SGM patients by healthcare providers is well-documented.