During the COVID-19 pandemic, medical schools were forced to suspend in-person interviews and transition to a virtual Multiple Mini Interview (vMMI) format. MMIs typically comprise multiple short assessments overseen by assessors, with the aim of measuring a wide range of non-cognitive competencies. The adaptation to vMMI required medical schools to make swift changes to their MMI structure and delivery. In this paper, we focus on two specific groups greatly impacted by the decision to transition to vMMIs: medical school applicants and MMI assessors. We conducted an interpretive qualitative study to explore medical school applicants' and assessors' experiences transitioning to an asynchronous vMMI format. Ten assessors and five medical students from one Canadian medical school participated in semi-structured interviews. Data was analyzed using a thematic analysis framework. Both applicants and assessors shared a mutual feeling of longing and nostalgia for an interview experience that, due to the pandemic, was understandably adapted. The most obvious forms of loss experienced - albeit in different ways - were: 1) human connection and 2) missed opportunity. Applicants and assessors described several factors that amplified their grief/loss response. These were: 1) resource availability, 2) technological concerns, and 3) the virtual interview environment. While virtual interviewing has obvious advantages, we cannot overlook that asynchronous vMMIs do not lend themselves to the same caliber of interaction and camaraderie as experienced in in-person interviews. We outline several recommendations medical schools can implement to enhance the vMMI experience for applicants and assessors.