Michelangelo created some of the most beautiful drawings of the Italian Renaissance for Tommaso de’ Cavalieri, a young Roman nobleman whom he met in 1532. Many of these drawings are well identified, but scholars have long debated which, if any, extant examples might be those mentioned by Vasari as idealized heads Michelangelo presented to Tommaso intended, at least in part, to help the young man learn to draw. Present attributions elicit considerable interpretive and stylistic challenges, especially in determining what Michelangelo might have meant to express with these images. This study takes a fresh look at one of the most controversial of these proposed attributions, the recto and verso of a sheet from the Royal Collection in Windsor Castle (RL 12764). Notable scholarly ambivalence concerns whether the so-called recto is male or female. We argue that the drawing is better understood by looking past binary distinctions of gender, in much the same way Michelangelo thought about Tommaso. The paper features a new identification of the helmet worn by the figure, which helps clarify Michelangelo’s intent. Finally, the paper reinforces how Michelangelo used drawings as opportunities for conversation, enabling a suggestive rather than literal form of communication between master and pupil, friend and friend, admirer and beloved.