In some circles of mathematics education, repetition and rote are somehow conflated in terms of their pedagogical uses and ramifications. In this paper, I argue for the separation of the two, relying upon a framework suggested by Martin Buber's "I-Thou" ontology. In the presentation of Buber's ideas, I highlight the notion of "will-as-would-join-with-grace," to be contrasted with plain "will". The merit of repetition in teaching and learning, as I argue, is not in automaticity--the common rationale--but in fostering and supporting a deepened sense of connection and/or intimacy to the object under study.