The meaning of Shakespeare's Sonnet 106 is relatively straightforward. The speaker is saying that, when he reads stories and poems in older books chronicling the beauty of "wights" gone by, he sees immediately that these ancient writers would have been eager to describe his own beloved with "their ancient pen." The beloved perfectly into the socially accepted idea of what is beautiful. Indeed, Shakespeare suggests that the older writers were merely anticipating, predicting, or "prefiguring" the arrival of his own beloved, as if he is the crowning glory of what is beautiful. However, the speaker fears that the skill of these poets, great as it was, was insufficient to capture the "wonder" of his beloved, given that even he, who is able to "behold these present days," feels hampered by the thought of adequately "prais[ing]" his young man.

There are some interesting implications in some of Shakespeare's language choices, however. The theme of the young man's androgynous beauty has pervaded the sonnets; elsewhere described as the "master-mistress" of the writer's "passion," we see again the suggestion that he is more beautiful than both men and women—and beautiful in a way that is both masculine and feminine—in that the speaker refers to both "ladies dead and lovely knights." The word "master," too, recurs here, suggesting that the beloved is able to direct or wield his beauty in such a way that it gives him power over others.

This connects to the idea of the beloved as singular, somebody anticipated and longed for, which is expressed here. He is cast by the speaker as a figure of prophecy, someone almost Messianic in that the speaker feels privileged to live at the same time as him, in "these present days." In Shakespeare's imagining the chroniclers of old attempting to "sing" and "praise" the young man, there is certainly a religious connotation. "Divining," too, is a word with a quasi-supernatural or religious connotation. The beloved, in the mind of the speaker, is not only a figure of "wonder," but a figure whose beauty is so supreme that it has been longed for and prophesied throughout all the long canon of "wasted time," making the beloved an almost godlike figure of "praise."