Unpacking middle school students' mathematical relationships is important as a step towards improving mathematical relationships. In this study, 500 middle school students drew personifications of mathematics. We examined these personifications of mathematics for insight into their relationships with mathematics. Using constant comparative methods, we present various ways the middle school students personified mathematics. Negative relationships were personified with terrible beasts, abusers, authoritarians, and pests/nuisances. Positive relationships were personified with best friends and nature. Some personifications supported both positive and negative relationships or were neutral relationships. Reflecting on these personifications point to components of positive relationships with mathematics that we should support and confronts ways we may be perpetuating negative relationships with mathematics. [For the complete proceedings, see ED630210.]