As Fermina Daza falls in love with her husband and becomes pregnant with her first child, Florentino Ariza works with his uncle at the riverboat company. His uncle is a kind and frugal man, and Florentino Ariza slowly makes his way up the ranks of the riverboat company, spending time at the lighthouse having affairs with women. He becomes an avid writer of love letters in the Avenue of Scribes in an earnest attempt to get rid of all the love in his system so he can write a reasonable business letter. Florentino has a few tumultuous love affairs—one with the girlfriend of a riverboat captain that ends with a robbery and threatening words on her apartment wall written by vandals. He falls in love with a plainly dressed woman during Carnival who admits to having escaped from an asylum, and during their evening together, she is captured by police and nurses.

As it turns out, she had decapitated a guard to escape in order to dance at Carnival. Florentino visits her at the asylum every week, with a box of chocolates and a perennial hope that he will see her through the barred windows.