The retrieval of traditional Christian contemplative practices such as centering prayer has continued steadily since the 1960s, although research into the effects of centering prayer has not kept pace. This study aimed to describe the practice effects of centering prayer through a comparative qualitative analysis of the accounts of three practitioners at different stages of practice (two, 10, and 23 years). Our hypothesis was that a “deepening” of experience will occur based on length of practice. Individual interviews were conducted using a fixed set of questions to initiate open-ended discussion. Using the fixed questions as categories enabled deductive thematic analysis comparatively across the three interviews, alongside an inductive reading of the content for themes outside the question categories. Acknowledging the serious limitations of the study, nevertheless suggestive confirmation of the “deepening” hypothesis was obtained that was also consistent with the literature on centering prayer and on meditation more broadly.