In "Sonnet 20," Shakespeare grapples with paradoxes, centering his poem on a man both masculine and feminine, powerful and powerless-the impossible object of a homosexual love that should not be. Through images of eyes and wealth veiled in double meanings, penned in the freeing and restricting form of a sonnet, we find that the subject's dual nature endows him with great power, yet the greatness of this power is what ultimately limits him.
If eyes are the windows to the soul, then the subject's eyes reflect a woman's heart, though brimming with aberrant power. Although a man, the poem's subject possesses feminine charms superior to a woman, with "An eye more bright than theirs, less false in rolling" (5). For one's eyes to be "bright" suggests one is free-spirited, lively and jubilant, unhindered by pain or hatred that might cloud the eyes. However, the word also connotes a quality of fairness and delicacy more often used to described women. Furthermore, it has advantage over the female eye in that it does not "roll", as if with madness or unfaithfulness. Temperateness and loyalty are two idyllic features in a lover, and it is in this gentle perfection as superior version of a woman that the subject finds his power-the power to "steal men's eyes" (8). Stealing someone's eyes implies a level of physical and sexual attractiveness; beyond having womanly attributes, the subject is physically feminine. Moreover, it involves having strong influence, for he can divert men from their former gaze upon women. Although his dual nature endows him this advantage, the tragedy is that he cannot act upon the power given to him because of his sexuality as a man.
The subject's blessings and difficulties are not limited to what his power attracts, but include that which it enables him to give-and power has made him most certainly wealthy. The strength of the subject's gaze is reinforced in line 6, where it is said to have a captivating sway over all it looks upon, "gilding the object whereupon it gazeth".