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It is illuminating to examine Michelangelo's poetry separately from his art, especially since during the peak of his poetic output, between 1532 and 1548, he also had some of his most significant personal experiences. Although arrogant about his artwork, Michelangelo's pride did not extend to his poetry, which he viewed with great humility. Michelangelo's earlier poetry is primarily made up of conventional forms like the courtly love poem, but in his later poetry Michelangelo began to explore the subjects of mortality and love.

The majority of his love poems date from the years when Michelangelo was in his fifties and sixties, and it is during this time that his struggle with his homosexuality is most pronounced. In the early 1530s, shortly after Michelangelo's move to Rome, he met a young man named Tommaso de' Cavalieri, to whom he dedicated numerous frustrated and intense poems and drawings of scenes from the Classical poet Ovid's writings on mythological love. Michelangelo left his poems ambiguously gendered, but, despite later editing by his heirs and by critics, Michelangelo clearly felt for Cavalieri an extreme level of erotic and romantic passion. The artist's poetic style resembles his visual work in energy, philosophical concerns, and in its constant sensuality and abandon. Many of these poems alter the Medieval traditions of heterosexual courtly love to better fit the context of homosexuality, which was not socially acceptable at the time. The twenty-three old Cavalieri, who was heterosexual and later married and had children–most notably, the composer Emilio Cavalieri–was not interested in the affections of the fifty-seven-year-old Michelangelo. The two became close friends for a time, until Cavalieri became uncomfortable with Michelangelo's obsession with him and distanced himself. Even after this separation, however, they remained in contact, and the devoted Cavalieri was present when Michelangelo died.

At this time Michelangelo also dedicated love poems to one or more anonymous subjects, who were probably simply poetic conceits. However, Vittoria Colonna, the marquess of Pescara, was certainly real, and she became an even closer friend of Michelangelo's than Cavalieri. Colonna's poetry and her zealous religious beliefs greatly influenced Michelangelo and led to his devout interest in Church reform. Although Colonna was apparently physically unattractive, she was the subject of many of Michelangelo's love poems, and she appears to have been the only woman with whom the reclusive artist ever had a serious relationship. When Colonna died suddenly in 1547 at the age of fifty-seven, Michelangelo was heartbroken, and her death ended the period of his greatest love poetry.

Other events likewise led to Michelangelo's withdrawal from poetry and his disillusionment with social relationships in general. The death of his friend and informal agent Luigi del Riccio in 1546 led to a reduction in the amount of poetry he wrote, as did his own illnesses from 1544 to 1546. He only wrote twenty-three poems after his death, all of them either laments on the effects of aging or touching meditations on the nature of death. Many of Michelangelo's later poems are directly addressed to Christ himself, and include desperate and guilty pleas for Michelangelo's spiritual salvation and the forgiveness of his sins.

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