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.