The young noble was exceptionally handsome, and his appearance seems to have fit the artist's notions of ideal masculine beauty, for Michelangelo described him as "light of our century, paragon of all the world".

In an official document translated by Gerda Panofsky-Soergel, mention is made that Cavalieri paid the stipend for the Mass in the memory of his brother Emilio on 6 September 1536.

It was noted that compared to his peers, Cavalieri did not participate in civic government extensively although he would serve in this position five times (in 1539, 1542, 1546, 1558, and 1562).

Cavalieri was made one of the Convervatori in 1554, taking the position responsible for supervising construction at the Campidoglio that Michelangelo had begun restorating in 1538.

Although his contemporaries commented on his good looks and cultivated nature, no definite image produced by Michelangelo of Cavalieri has survived.

According to Cavalieri, they were united by a mutual love for art, and the letter refers to "Those works of mine that you have seen with your own eyes, and which have caused you to show me no small affection".

[11] According to Gayford (2013), "Whatever the strength of his feelings, Michelangelo’s relationship with Tommaso de'Cavalieri is unlikely to have been a physical, sexual affair.

Even if we do not choose to believe Michelangelo’s protestations of the chastity of his behaviour, Tommaso’s high social position and the relatively public nature of their relationship make it improbable that it was not platonic".

The meaning of the drawings is not fully understood, although it is common for scholars to relate them to moralizing themes or ideas about Neoplatonic love.

He attempted to rape a goddess and was killed by two of the deities, but his punishment did not end with death; for eternity he was chained to a rock in Hades while two vultures ate his liver, which was considered the seat of the passions.

[15] Zeus lusted after Ganymede, the most beautiful of all humans, and turned himself into an eagle to abduct him to serve the god at Mount Olympus, or to rape him.

[16] On another version of the composition, today in the British Museum,[17] Michelangelo wrote a note to Cavalieri: "Master Tommaso, if this sketch does not please you, tell Urbino so that I have time to do another by tomorrow evening, as I promised you.

[19] Some modern commentators assert that the relationship was merely a platonic affection, even suggesting that Michelangelo was seeking a surrogate son.

In 1893, an early British homosexual activist, John Addington Symonds, wrote a two-volume biography of the artist and he undid this change in his translation into English of the original sonnets.