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In higher education, Learning Assistants (LAs)—a relatively recent evolution grounded in peer mentorship models—are gaining popularity in classrooms as universities strive to meet the needs of undergraduate learners. Unlike Teaching Assistants, LAs are undergraduate students who receive continuous training from faculty mentors in content-area coaching and pedagogical skills. As near-peers, they assist assigned groups of undergraduates (students) during class. Research on LAs suggests that they are significant in mitigating high Drop-Fail-Withdrawal rates of large enrollment undergraduate science, technology, engineering, mathematics, and medical (STEMM) courses. However, there is a dearth of description regarding the learning between LAs and STEMM faculty mentors. This paper reports on perspectives of faculty mentors and their cooperating LAs in regard to their learning relationships during a Calculus II at a research-oriented university during Spring of 2020. Using an exploratory-descriptive qualitative design, faculty (oral responses) and LAs (written responses) reflected on their relationship. Content analysis (coding) resulted in four salient categories (by faculty and LA percentages, respectively) in: Showing Care and Fostering Relationships (47%, 23%); Honing Pedagogical Skills (27%, 36%); Being Prepared for Class and Students (23%, 28%); and Developing Content Knowledge in Calculus (3%, 13%). Benefits of LAs to faculty and ways to commence LA programs at institutions are also discussed.