Sonnet 136 has been used by scholars to cast the sonnet sequence as autobiographical, since the speaker implies his name is Will. The speaker is also playing on the variety of meanings of “will”—including genitalia and lovers—in order to comment on the lady’s promiscuity. The speaker also draws on the other meanings of “will” to associate himself with the sexual satisfaction he believes the dark lady craves. If it is sex that she wants, then she must love him, because his name itself contains and suggests those amorous activities.

In Sonnet 136, the speaker continues to play with the word “will” as he implores the dark lady to accept him back into her graces. The speaker extends the suggestion that since the dark lady has many lovers, the addition of the speaker would be inconsequential. The conceit of numbers and quantities leads into a double entendre in the final four lines. In Elizabethan England, “nothing” and “something” were slang terms for genitals. On the surface, the speaker encourages the dark lady to view him as inconsequential, but by referring to himself as “nothing me” who is “a something sweet to thee,” he adds a sexual context to his humble advances.

In contrast to the praised “mourning eyes” from the previous sonnet, the mistress’ eyes have now become “cruel” due to her affair with the speaker’s “next self,” a close friend of his who is often interpreted to be the fair youth. Her cruelty is thus twofold in that she has infatuated both the speaker and the fair youth. Prior to the affair, the speaker could look at the youth as an ideal of purity. Furthermore, since the speaker views the youth as an extension of his own soul, the youth could guard what was left of the speaker’s sense of personal innocence while indulging his lust with the dark lady. However, now that the youth is also involved with the dark lady, the speaker’s purity has been entirely forsaken.

In Sonnet 140, the speaker resorts to threatening the dark lady with public slander unless she pretends to love him. The diction of Sonnet 140 features words related to health, such as “sick,” “death,” “physician,” “madness,” and “ill.” This serves to characterize love as a sickness that has deteriorated the speaker’s mental state. Just as “testy sick men” only want good news from their doctors, the speaker only wants to hear faithful and loving things from the dark lady. Even if she doesn't actually love him, the speaker asks that she pretend that she does. Otherwise he will “speak ill” of her in his madness, which he claims is wrought by her “disdain.”

Sonnet 139 opens with the speaker’s refusal to defend the dark lady’s actions. However, he relents in the third quatrain and excuses her indiscretions by saying that she looks at other men in order to spare the speaker from the “injuries” caused by her “pretty looks.” The speaker’s defences are “o’erpressed’d,” or overburdened, and cannot withstand the “might” of the lady, adding a violent valence to their relationship as the lady lays siege to the speaker’s emotions. The lady’s infidelity continually “wounds” the speaker, so rather than continuing to make a show of looking at other men in his presence, he urges her to “kill [him] outright” by admitting to her affairs.

The Roman God of love, Cupid, was often depicted wearing a blindfold. The metaphor of love being blind has endured throughout the years, expressing how lovers often don’t see the flaws in their loved ones—at least not at first. However, the speaker has never pretended that his mistress was beautiful or good. In his case, he was willfully blind, overlooking her flaws in favor of indulging his lust. Now that she has apparently rejected him, he questions whether it was his eyes or his heart that led him to ignore her poor character. In Sonnets 46 and 47, the speaker describes his eyes and heart as being at “mortal war,” eventually reconciling to become partners in love. However, in Sonnet 137, both become objects of blame instead.

The word “will” is used thirteen times in Sonnet 135, opening the poem up to a layered interpretation due to the multiple potential meanings of “will.” “Will” can mean desire, determination, or lust. It can also refer to the genitals of any gender. “Will” is also a shortening of the name William, Shakespeare’s own name. Sonnet 135 is most often read as a lover’s plea, with an alternate interpretation as an unflattering mockery of the lady’s promiscuity. The speaker beseeches the dark lady to allow him back into her graces, referring to the multiple “wills” in her possession, which likely refer to either her other lovers or her sexual insatiability, or both. The speaker asks why a woman with such a large “will” and with so many other “wills” at her disposal cannot accept one more—the speaker’s own.

Sonnet 134 is a continuation of Sonnet 133. The speaker employs a combination of legal and financial diction to give the love between himself, the lady, and the youth a transactional cast. The dark lady is described as a “usurer,” or moneylender, whose currency is sexual in nature. When paired with the idea of a mortgage, the speaker’s offer to “forfeit” himself refers to the act of signing himself over to the lady to pay the youth’s debts. However, the speaker knows the lady will not give up the youth and laments his involvement. The closing couplet takes on a despairing tone: the fair youth is paying both his own debts and the speaker’s, leaving the speaker free from obligation but not from his attraction to the lady.

Sonnets 40 to 42 and Sonnets 133 and 134 are thought by many to discuss the same situation as Sonnet 133, wherein the fair youth and the dark lady become entangled, leaving the speaker estranged from both of them. Notice that in both sets of poems, the speaker prioritizes the loss of the youth over the loss of the mistress. In order to protect the heart of the youth, the speaker offers to let himself be imprisoned in the “steal bosom” of his mistress so long as he is allowed to “guard” the youth. However, the speaker admits that the mistress controls him completely and that his heart makes a poor guard for the youth, since she owns both him and “all that is in” him.

The noun “ruth” refers to feelings of pity or distress. Pity from a mistress, usually expressed in the form of physical intimacy, was a common request in the sonnet tradition. Male speakers with aloof mistresses would bemoan the lack of reciprocity for their passions, urging their mistresses to take pity on them and engage in amorous activities. However, as opposed to the aloof beauties of the sonnet tradition, the speaker’s dark mistress lacks conventional beauty. She is made attractive by her “mourning eyes” and “pity” for the speaker, perhaps implying that her willingness to engage in physical intimacy is what draws the speaker to her.

Eyes are commonly depicted as the medium through which love flows. In Act II, Scene II of Shakespeare’s The Merchant of Venice, as Bassanio attempts to solve Portia’s riddle, she sings about where love is born from, and the answer is that “it is engendered in the eyes.” Sonnet 132 echoes Sonnet 127 when it praises the lady’s eyes as “black and loving mourners.” Notice the repetition of the theme of “mourning.” In Sonnet 127, the eyes were mourning the death of beauty, but in Sonnet 132 they seem to be mourning the speaker himself.

In Sonnet 131, the speaker rejects the notion that the dark lady is not beautiful enough to inspire love. He puts forward his “thousand groans” as proof that she has captured his “dear doting heart.” Groaning is commonly used in literature to represent lover’s pain, so the fact that the dark lady has inspired so many groans proves that she is beautiful enough to inspire love. For the groans to be “one on another’s neck” means that they are continuous, indicating that the speaker is able to think of little else but the lady. However, even if the speaker finds beauty in her looks, her “deeds” are less fair and, at least according to the speaker, lead to the “slander” about her appearance.

Sonnet 138 deals with the common literary trope of transgression and lying. The speaker readily admits in the first line that he knows his lover is lying, but he stays quiet and the “truth [remains] suppressed.” However, he admits that he is lying as well. At the end of the sonnet, the speaker employs a double entendre to highlight how he and his love “lie” together and therefore feel mutually “flatter’d” despite their obvious faults.