This section takes its title from two plays by the early 17th-century playwright Thomas Middleton, in one of which the moves in a game of chess denote stages in a seduction. This section focuses on two opposing scenes, one of high society and one of the lower classes. The first half of the section portrays a wealthy, highly groomed woman surrounded by exquisite furnishings. As she waits for a lover, her neurotic thoughts become frantic, meaningless cries. Her day culminates with plans for an excursion and a game of chess. The second part of this section shifts to a London barroom, where two women discuss a third woman. Between the bartender's repeated calls of "HURRY UP PLEASE IT'S TIME" (the bar is closing for the night) one of the women recounts a conversation with their friend Lil, whose husband has just been discharged from the army. She has chided Lil over her failure to get herself some false teeth, telling her that her husband will seek out the company of other women if she doesn't improve her appearance. Lil claims that the cause of her ravaged looks is the medication she took to induce an abortion; having nearly died giving birth to her fifth child, she had refused to have another, but her husband "won't leave [her] alone." The women leave the bar to a chorus of "good night(s)" reminiscent of Ophelia's farewell speech in Hamlet.

The first part of the section is largely in unrhymed iambic pentameter lines, or blank verse. As the section proceeds, the lines become increasingly irregular in length and meter, giving the feeling of disintegration, of things falling apart. As the woman of the first half begins to give voice to her paranoid thoughts, things do fall apart, at least formally: We read lines of dialogue, then a snippet from a nonsense song. The last four lines of the first half rhyme, although they are irregular in meter, suggesting at least a partial return to stability.

The second half of the section is a dialogue interrupted by the barman's refrain. Rather than following an organized structure of rhyme and meter, this section constitutes a loose series of phrases connected by "I said(s)" and "she said(s)." This is perhaps the most poetically experimental section of the entire poem. Eliot is writing in a lower-class vernacular here that resists poetic treatment. This section refutes the prevalent claim that iambic pentameter mirrors normal English speech patterns: Line length and stresses are consistently irregular. Yet the section sounds like poetry: the repeated use of "I said" and the grounding provided by the barman's chorus allow the woman's speech to flow elegantly, despite her rough phrasing and the coarse content of her story.

The two women of this section of the poem represent the two sides of modern sexuality: while one side of this sexuality is a dry, barren interchange inseparable from neurosis and self-destruction, the other side of this sexuality is a rampant fecundity associated with a lack of culture and rapid aging. The first woman is associated by allusion with Cleopatra, Dido, and even Keats's Lamia, by virtue of the lushness of language surrounding her (although Eliot would never have acknowledged Keats as an influence). She is a frustrated, overly emotional but not terribly intellectual figure, oddly sinister, surrounded by "strange synthetic perfumes" and smoking candles. She can be seen as a counterpart to the title character of Eliot's earlier "Love Song of J. Alfred Prufrock," with whom she shares both a physical setting and a profound sense of isolation. Her association with Dido and Cleopatra, two women who committed suicide out of frustrated love, suggests her fundamental irrationality. Unlike the two queens of myth, however, this woman will never become a cultural touchstone. Her despair is pathetic, rather than moving, as she demands that her lover stay with her and tell her his thoughts. The lover, who seems to be associated with the narrator of this part of the poem, can think only of drowning (again, in a reference to The Tempest) and rats among dead men's bones. The woman is explicitly compared to Philomela, a character out of Ovid's Metamorphoses who is raped by her brother-in-law the king, who then cuts her tongue out to keep her quiet. She manages to tell her sister, who helps her avenge herself by murdering the king's son and feeding him to the king. The sisters are then changed into birds, Philomela into a nightingale. This comparison suggests something essentially disappointing about the woman, that she is unable to communicate her interior self to the world. The woman and her surroundings, although aesthetically pleasing, are ultimately sterile and meaningless, as suggested by the nonsense song that she sings (which manages to debase even Shakespeare).

The second scene in this section further diminishes the possibility that sex can bring regeneration--either cultural or personal. This section is remarkably free of the cultural allusions that dominate the rest of the poem; instead, it relies on vernacular speech to make its point. Notice that Eliot is using a British vernacular: By this point he had moved to England permanently and had become a confirmed Anglophile. Although Eliot is able to produce startlingly beautiful poetry from the rough speech of the women in the bar, he nevertheless presents their conversation as further reason for pessimism. Their friend Lil has done everything the right way--married, supported her soldier husband, borne children--yet she is being punished by her body. Interestingly, this section ends with a line echoing Ophelia's suicide speech in Hamlet; this links Lil to the woman in the first section of the poem, who has also been compared to famous female suicides. The comparison between the two is not meant to suggest equality between them or to propose that the first woman's exaggerated sense of high culture is in any way equivalent to the second woman's lack of it; rather, Eliot means to suggest that neither woman's form of sexuality is regenerative.