This paper attempts to highlight the complexities, challenges and dilemmas for one educator in adopting a pedagogy of relation in Higher Education (HE). The agenda of HE focused primarily on globalisation, accountability, employability and quality assurance has created an overly transactional relationship between students and teachers. In doing so, we become tasked with valuing what can be measured rather than measuring what we value. Often absent in the discourse around student success in HE is the importance of the teacher-student relationship. Through the analysis of my diary over the course of a year, I captured daily incidents and reflections to gain a deeper understanding of my practice as relational. They revealed vulnerability to be at the core of these experiences. The contradicting power dynamics between students, staff, organisation and stakeholders, created dilemmas in how to respond to this vulnerability. Here, I share my analysis of three significant examples of practice where the need to embrace vulnerability was essential for a pedagogy of relation but where they were met with resistance. This dynamic response to relational practice in the personal, social and cultural space of higher education, I describe as a ‘pedagogy of vulnerability’. I hope that through sharing my experiences and dilemmas, it can open up a dialogue which raises the importance of the teacher-student relationship and how to adjust the systems and cultures to enact a pedagogy of relation in higher education.