Using an interdisciplinary, post-qualitative, pedagogical methodological (Burke, Crozier, and Misiaszek 2017) practice of "timescapes" (Adam 1998, Burke 2018a), I explore my longest teaching/mentoring relationship, spanning two decades. I conceptualize this process as a post-qualitative encounter (Davies et al. 2013). The first half of the paper explores higher education teaching/mentoring through this "timescapes" practice, incorporating studies across higher education, gender, gerontology and the humanities. In the second half, I present four critical conjunctures in this teaching/mentoring relationship. Ultimately, I argue that expanding what is understood by the concept of a 'teaching/mentoring relationship', particularly through studies of long-term relationships and through practices such as "timescapes encounters," is a powerful counter-hegemonic tool in the face of neoliberal pressures and measures of impact in teaching in higher education.