As fate would have it for Ben, his pale complexion after being released from jail gave him the benefit of another attempt to escape, and this time he was successful. As for Jacobs herself, she began to draw the eye of Dr. Flint, who began to make overtures to Jacobs to begin a more physical relationship. Jacobs refused; however, no harm was to fall upon her on orders of Flint. Nonetheless, Mrs. Flint seemed privy to what was going on, and enquired to Jacobs the specifics of the relationship. Dr. Flint became more and more agitated with Jacobs denials, and even struck her for the first time. Eventually though, Jacobs became pregnant with her lover's child, and brought shame to her family. Her grandmother shunned her, and there was no consolation among the slaves toward her, only pity. Her master, on the other hand, sought to have her say whether the child was born of a black man, or of a white man. Jacobs never gave in to his wishes, and would later bear a premature child. Dr. Flint's incessant mental torture was soon there after the birth to constantly remind her that her life was to be spent as a slave, and that now her child was to be a slave for life. Fortunately, in Jacobs mind, the child was a boy, and although Jacobs would sometimes wish that the child would've died than face a life of slavery, it was more fortunate for the child to be a boy than a girl. .
Jacobs recounts on the propaganda that slaveholders told slaves of the North. The North was seen as a haven for freedom, and a place where all slaves should hope to go, their "Promised Land". However, it was in the slaveholders" intentions to make sure that the North was seen as anything but a Promised Land. Great attempts were made to show that runaways who made it to the North faced near starvation and even more harsh conditions than they had faced in captivity. These accusations were obvious lies to those who had family or friends in the North who would inform slaves on what conditions in the North actually were.