It is impossible to know for certain whether Michelangelo had physical relationships (Condivi ascribed to him a "monk-like chastity"),[60] but the nature of his sexuality is made apparent in his poetry.[61] He wrote over three hundred sonnets and madrigals. The longest sequence was written to Tommaso dei Cavalieri (c. 1509–1587), who was 23 years old when Michelangelo met him in 1532, at the age of 57. These make up the first large sequence of poems in any modern tongue addressed by one man to another, predating Shakespeare's sonnets to the fair youth by fifty years:
I feel as lit by fire a cold countenance
That burns me from afar and keeps itself ice-chill;
A strength I feel two shapely arms to fill
Which without motion moves every balance.
— (Michael Sullivan, translation)