On the day that Florentino first sees Fermina since her return from Europe, he resolves to earn the status necessary to deserve her. Florentino decides that for their love to abound, Dr. Juvenal Urbino must die, a death for which Florentino will wait without impatience or violence. Uncle Leo XII, President and Manager of the River Company of the Caribbean, gives Florentino a menial job as a clerk, writing official documents. Even Florentino's business letters are poetic, and his uncle reprimands him for his literariness. Despite his efforts, Florentino cannot write anything but poetry, and is reassigned to pick up trash, though his uncle promises to promote him. After thirty years, Florentino has moved through every post in the company.
Florentino offers his services as a poet to people in the marketplace. He fondly remembers how one customer, a young girl, had asked him to write a reply to a love letter he had just penned. The correspondence continued between the lovers through Florentino; eventually, the couple marries. After realizing he had been their mutual scribe, the couple asks that Florentino be the godfather of their first child. Florentino compiles a book, Lover's Companion, though it is so long that no printer will accept it.
Transito Ariza buys and restores their entire house in preparation for Fermina's arrival. After its completion, Transito is diagnosed with an incurable disease. Meanwhile, Florentino frequents the transient hotel, sometimes bringing along his friends. Florentino's already tarnished reputation worsens when people notice that he and his male friends do not go to the bar, but to a room. Florentino stops visiting the hotel, and instead takes women to various public places. His favorite is the lighthouse.
Florentino meets fifty-year-old Ausencia Santander when her husband, his colleague, brings him to lunch. Florentino is more attracted to her house than to Ausencia herself, but after they drag her drunken husband to bed, they go to bed themselves, and continue their affair for seven years. One afternoon, Florentino feels as if he is being watched, and tells Ausencia so. Naked, she leaves the room for a drink, and screams when she discovers that all of her belongings have been stolen. On the wall, a message reads: "This is what you get for fucking around." Her husband never understands why she does not report the robbery.
After the theft, Florentino does not visit Ausencia as often. He rides a trolley on which he picks up "free-flying little birds." One such bird has escaped from the insane asylum and is on the loose after having decapitated a guard and wounded two others. Florentino does not discover this until, after having danced with her all night at the carnival, she is seized by two guards and a nurse. Heartbroken, he stands outside the asylum with chocolates, hoping to see her, though he never does.
Florentino meets another woman on the trolley, Leona Cassiani. She stares at him, and though she is a beautiful black young woman, he thinks her a whore. When he leaves the trolley, she follows him until he turns around to tell her that he does not pay for sex. She replies that he certainly does; it is evident in his face. Leona, however, does not want sex; she wants employment. Florentino says that mistaking Leona for a whore is his life's worst mistake. He takes her to the head of Personnel, who gives her the lowest-level job at the River Company.