It is long evident that college campuses have been evolving considerably. Adult learners play a key and welcome role, challenging assumptions about formal learning and its delivery, with institutions themselves re-assessing long-held beliefs and procedures, protocols and hierarchies, participation and roles of both student and faculty alike, and the reciprocal relationship between them. People in the academic community profoundly affect students and their perceptions of an institution and the faculty comprising it. Retention success or failure may be tied strongly to the co-created key student/professor relationships, but not solely those within classroom or academic advising contexts. Connecting with students from the outset and being mindful of their progress beyond the immediate concerns of course completions and degree requirements can influence goodness of fit, based as it is on a host of elements big and small, personal and impersonal. The author approaches this topic as a recent midlife student himself, but now college teacher. The author believes that fresh participation from both sides may help shed light on this potentially delicate, perhaps ignored, but nonetheless important relationship between teacher and student, prompting further thought and response.