Sonnet 144 is the only sonnet that explicitly refers to both the Dark Lady and the young man, the poet's "Two loves." Atypically, the poet removes himself from the love triangle and tries to consider the situation with detachment. The humor of the previous sonnet is missing, and the poet's mood is cynical and mocking, in part because uncertainty about the relationship torments him.
Although the sonnet is unique in presenting the poet's attempt to be objective about the two other figures in the relationship, stylistically it is very similar to others in terms of setting up an antithesis between two warring elements, the youth ("comfort") and the woman ("despair"): "The better angel is a man right fair, / The worser spirit a woman, colored ill." Symbolically, the young man and the woman represent two kinds of love battling for supremacy within the poet's own character: selfless adoration and shameful lust, respectively. However, the poet is a mere spectator now. His greatest fear, one that he cannot face, is that the young man secretly acquiesces to the woman's advances: "And whether that my angel be turned fiend / Suspect I may, yet not directly tell." Unfortunately for the poet, what the outcome of this struggle will be is uncertain: "Yet this shall I ne'er know, but live in doubt, / Till my bad angel fire my good one out." Just what the phrase "fire my good one out" means is debatable. One critic suggests that the phrase means "until the woman infects the youth with venereal disease"; others offer the more innocuous meaning "until the youth grows tired of the woman." Ironically, the uncertainty about the fate of the relationship between the young man and the woman is the only certainty the poet has.