Being a first time researcher conducting semi-structured conversational interviews for a PhD, I thought I was prepared for any story or discussion that would occur. My participants were adults who have dyslexia and I was asking them to recall their educational experiences, and how they perceive them to have impacted on their life choices. Having already established a relationship with the selected participants in a previous context as their lecturer, nobody had prepared me for the emotional roller coaster I was about to ride during the interview process as an ‘insider’. I have identified five unexpected types of encounters that occurred in the course of the interviews that made me more of an active participant than an observer in their life stories and made me question my role in the research process. These encounters I have identified as (1) The Sad encounter; (2) The Unexpected Proximity encounter; (3) The Language Processing encounter; (4) The Empathetic encounter; and (5) The Boy Scout – Be Prepared Encounter. On reflection and analysis of the interviews these encounters have shaped the responses not only of the participants but also of myself. How has this occurred and how have the encounters influenced and shaped the responses of the participants? More importantly, as the researcher, whose story is really in my head during the interviews? Will my personal interactions and stories influence the final outcome in terms of the representations of their stories?