In the first paragraph of his narrative, Douglass expresses reluctance to disclose the identities of the white boys who assisted him in learning to read, deeming it a nearly unforgivable transgression

In the first paragraph, Frederick Douglass emphasizes that naming the white boys who taught him to read would be an "almost unpardonable offense". This was due to the societal norms of the time, which severely penalized both blacks learning to read and whites teaching them. However, Douglass also adds a personal comment saying, "Learning to read had been a curse rather than a blessing," illustrating the anguish and frustration that educational enlightenment brought unto him. This knowledge had made him more acutely aware of the severity of his enslavement, therefore invoking more pain rather than pleasure. Later, when he reads one of Sheridan's speeches in "The Columbian Orator," he becomes particularly struck by the idea of freedom and human rights. He is able to draw distinctions between his current state of bondage and the world of freedom advocated by Sheridan—a world where people are treated as equals and not discriminated against due to the color of their skin. The newfound understanding stand as a testament to the duality of his education: it both enlightens and torments him. It is enlightening insofar as it broadens his understanding of the world and human rights, yet tormenting as it emphasizes the tragic reality of his condition as a slave.