Oedipa travels back to Berkeley after noticing that the original copy of the Wharfinger play was different from the version she saw because her paperback copy did not contain any line about Tristero. A footnote explained that the difference may have been related to a particular printing error, but Oedipa decides that she needs to meet with Emory Bortz, an English professor at UC- Berkeley who wrote the preface to the revenge play anthology. She hopes that Botz can explain the differences between the three or four different versions of the play (the Quarto version, the Folio version, and the "Whitechapel" version). She finds, however, that Bortz has moved to San Narciso College, but before going there, Oedipa stops by the residence of John Nefastis to see his machine. She tells Nefastis that Koteks said that Nefastis would be able to test Oedipa to see if she was a "sensitive." Nefastis explains the scientific foundations for entropy and how the Nefastis Machine theoretically works. Entropy, says Nefastis, connects thermodynamics and information flow. The Maxwell's Demon uses both. Nefastis leaves Oedipa to see if she can communicate with the Demon, forcing it to sort molecules by exerting only her mental affinity. Her attempt fails, however, and Oedipa realizes she is not a "sensitive." Nefastis, unfazed, comes out and invites her to have sex with him, but she runs out screaming.
Oedipa has come to believe that the Tristero is her own personal Maxwell's Demon because the Tristero holds "everything" together in her mind. It is the center of her obsession. She reflects on all the different pieces of the mystery she is trying to untangle: the Thurn and Taxis system, the muted post horn, the existence of the sign in the United States before 1853, the men who dressed as Indians to fight Wells Fargo and the Pony Express, and the fact that the organization seems to still exist in California. While thinking, Oedipa decides to wander around randomly, beginning what will be a very long night. She first finds herself being herded into "The Greek Way," a gay bar, where she meets a man with the Tristero symbol on a button in the lapel of his coat. He refuses to give her any information about Tristero even after Oedipa tells him absolutely everything she has learned so far. He does, however, tell her that "Kirby," the name she saw scrawled under the muted horn in the bathroom of The Scope, is a code name. He also informs her that his pin indicates that he is a member of Inamorati Anonymous, a take-off on Alcoholics Anonymous that seeks to help people overcome their addiction for falling in love and getting emotionally wounded. The man says that love is "the worst addiction of them all." He relates the esoteric story of how the group was founded, leaving Oedipa with the idea that the muted horn now stands for two different groups.
As we see in this chapter, this novel thematically treats a blend of many different cultural fragments, and one of the ways it does so is by writing about many different levels of society. This book discusses in detail the culture of suburbia, hippies, colleges, theater, Jacobean Europe, academia, medicine, and conspiracy groups, to name only a few. One of Pynchon's strong suits is his ability to piece together all these fragments into one logical order, all the while questioning the legitimacy and efficacy of the ordering impulse itself.
The idea of a fragmented society and the problems of integration is a great literary concern of the 20th century. Social fragmentation was raised most prevalently by T.S. Eliot, whose long poem The Waste Land is a type of collage of fragments taken for every corner of global intellectual history. Eliot's emphasis lies in blending the past and the present together to show the deeper underlying universal features of the human experience. Eliot wrote that nothing is lost upon a true poet; a poet must have the ability to absorb all parts of culture and experience, which means being able to think about Shakespeare while enjoying the beauty of a sunny day at a picnic with a loved one watching the animals nearby. The poet Wallace Stevens took a similar interest in cultural fragmentation in his poem "Man on the Dump," which deals with a character who sits atop a garbage heap watching all parts of discarded culture thrown together in one big mess. The American novelist Saul Bellow wrote the novel Herzog to address in narrative form the fragmentation of society and the problems of coming to terms with all types of experience in such a chaotic world. Pynchon's The Crying of Lot 49 clearly fits within this well-grounded tradition. Oedipa's search for order mimics the question put forth by the Fisher King at the end of Eliot's The Waste Land: "Shall I put my lands in order?" Oedipa is a very typical 20th-century figure, living at the center of chaotic experience and trying to put things "in order" or at least make sense of the world in which she must live.
Another 20th-century motif in The Crying of Lot 49 relates to sexual liberation. Notice that early in the novel, Oedipa has an affair with a man she barely even knows solely for erotic enjoyment and out of a general sense of boredom with her marriage. The affair is casual to the extreme, but most interesting is the fact that it comes out of the inability to maintain a stable relationship with the man to whom she is supposed to be faithful. Once again, the communication breakdown motif enters the narrative (albeit indirectly). Oedipa's affair is more than anything else a way of lessening boredom, which is indicative of a reduction in cultural values related to sex. Likewise, Nefastis seems to proposition Oedipa for no reason other than to achieve sexual satisfaction as a means of relieving boredom. Again, the tie-ins to Eliot's The Waste Land, which features characters who have sex only to relieve boredom, are very substantial. This novel of the 1960s seems to indicate that sex is not the intensely sensuous, emotionally driven, passionate experience that it was to writers like DH Lawrence. Rather, it has lost much of its import and significance.
Finally, it is important to recognize that Oedipa is becoming increasingly (and dangerously) isolated from other people. The most pristine image of this isolation comes early in chapter five, when Pynchon writes, "Oedipa sat, feeling as alone as she ever had, now the only woman, she saw, in a room full of drunken male homosexuals." She cannot even relieve her boredom and isolation by engaging in sex, which is ruled out by the homosexuality of her company. She has withdrawn from her husband, her physician, and even her lover. Her social world is disintegrating along with the culture in which she lives. This theme will become even more pronounced in upcoming sections. Oedipa's withdrawal and final isolation is one of the most pessimistic features of the novel.