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.
After three years, Leona is promoted when she impresses Uncle Leo, who appoints her his personal assistant. He endearingly calls her "my namesake Leona." In the following years, Leona takes control of the company, though she refuses to accept a higher position because it is only one step below Florentino. Secretly, he often regrets that she had not been a whore; in the ten years he has known her, he has not propositioned her. One night, when they are alone in the office, Florentino asks her when they are going to stop playing games and cut to the chase. Leona replies that she has been waiting ten years for him to ask her, but that since she loves him so much, she would feel as if she were going to bed with her son. Florentino withdraws, and eventually feels compelled to reveal the secret of Fermina Daza to Leona, but with proper opportunity.
Florentino, whether consciously or not, is driven to better himself because he feels that he is severely inferior to Dr. Urbino. The doctor impresses everyone with his vast medical knowledge, public renown, honorable endeavors, and prestigious degrees. Dr. Urbino poses an obstacle to Florentino's seemingly futile pursual of Fermina, serving as a roadblock on an already treacherous path. Florentino's perseverance is more proof of his obsession with Fermina. In challenging himself to raise his own standards, and, in doing so, others' opinions of him, Florentino creates somewhat of a contest; he pits his former self against the successful self he wants to be, and, meanwhile, engages in a non-violent, however persistent battle against the prestigious Doctor.
When Florentino decides that Dr. Urbino must die before his love for Fermina can be requited, his decision is not malicious. He understands Dr. Urbino and the obstacle he presents as a conceptual, factual problem that can only be solved when it is completely eliminated. Florentino realizes that for as long as he is alive, Dr. Urbino will block him from Fermina's heart. However, Florentino is a man of gentle nature, and understands that he must wait until the Doctor dies a natural death so that he may be with Fermina. It is only when Florentino accepts Dr. Urbino as a factual, indestructible obstacle that he can see past the problem, for it is then that he is able to discern a feasible solution. His solution is to obtain wealth and status that surpass or equal the Doctor's. Florentino is continually intimidated by the Doctor's wealth, status, and public renown. He aspires to surpass the Doctor in every way he can, for he may not be able to call himself Fermina's husband, or even the object of her affections, but he can, however, pledge to attain the status, income, and public renown that will elevate him to the social level on which Dr. Urbino's reigns.
Driven by his desire to be worthy of Fermina, Florentino excels in the company, attaining status and financial wealth, though he never can attain the public renown to match that of Dr. Urbino. Instead, Florentino's reputation among the people of the city is that he is a peculiar fellow, with odd habits, proper manners, and a somber mood. Although he has many liaisons with many different women, Florentino does not want rumor to circulate that he sleeps with as many women as he does, for he does not want to ruin himself in Fermina's eyes. To have Fermina believe that Florentino gives his love to other women would devastate Florentino far more than Fermina's regular dismissal of him would.
Notes on Chapter Two contain an error. Florentino Ariza is not the man with whom the girls held lotteries to hang out with, until he saw Fermina Daza; that was Dr. Juvenal Urbino. See the first paragraph in Chapter 3 to see where this sentence refers to the latter.
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Actually, women held lotteries to hang out with both men. When Florentino is introduced in chapter 2 Marquez mentions this on page 54. Then again, on page 105 (the first page of chapter 3), the lotteries for Dr. Urbino are mentioned.
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