During her teen years, Harriet became romantically involved with a free-born carpenter whom she had known since childhood. He proposed marriage, but Harriet had little faith that she would be allowed to become his wife. She also knew that Dr. Flint would not consent to her lover’s offer to buy her. Mrs. Flint would have been of no help here either. Though Mrs. Flint would have been happy to be rid of Harriet, Mrs. Flint didn’t believe that enslaved people were entitled to families of their own.

One day, Dr. Flint summoned Harriet to his study. He knew about her wish to be married and insisted that she marry one of the enslaved workers on his plantation. Harriet refused, saying that all men are not alike. When Dr. Flint asked if she loved the carpenter, Harriet replied that she did. Dr. Flint derided the carpenter, but Harriet countered that the man whom he called a “puppy” never insulted her and would not have loved her if she were not virtuous. This response prompted Dr. Flint to strike Harriet for the first time. He reminded her that he could do with her as he pleased, which Harriet refused to accept. After he threatened to send her to jail for insolence, Harriet told him that she would have greater peace there. Dr. Flint ended the conversation by telling her that he would never allow her to marry and that, if he spotted her lover on his property, he would shoot him.

After ignoring Harriet for two weeks, Dr. Flint passed her a note apologizing for hitting her but blaming her for his loss of temper. He would be going to Louisiana and wanted her to accompany him. Harriet refused to go on the trip.

In the autumn, Dr. Flint’s oldest son went to Louisiana to look at property. He returned with an unfavorable report, leaving Dr. Flint to abandon the prospect. Meanwhile, Harriet resumed meeting her lover in the street. When Dr. Flint saw them, he showered threats and insults upon her. Harriet resolved that she could never marry her lover. She told him not to return to visit her and advised him to go to the Free States. He obeyed and left.

Enslavers, Harriet notes, loved to tell lies about the North. They regaled their workers with fabrications about self-liberated individuals living in deplorable conditions. One such enslaver told Harriet that he had seen a friend of hers in New York, dying of starvation. Later, after Harriet’s own escape, she stayed with that friend in New York and found her living comfortably.

When talking of the North, Southerners “[indulged] in the most contemptuous expressions about the Yankees, while they, on their part, [consented] to do the vilest work for them” (73). Northerners, Harriet observes, were not welcome in the South if they disagreed with slavery. Northerners who adopted Southern ways tended to become “the hardest masters” (73).

A country planter whom Harriet calls Mr. Litch “was an ill-bred, uneducated man, but very wealthy” (76). He owned 600 enslaved workers whom he could not tell apart. Overseers managed his plantation, which also held a jail and a whipping post. He was so protected by his wealth that no crime committed on his property was punished—even murder, which was common there. An enslaved man who stole food was bound in chains and imprisoned. That man remained in prison until he thinned from hunger and deprivation.

The plantation owner’s brother was just as cruel though not as wealthy. He kept and trained bloodhounds specifically for the purpose of hunting workers who sought freedom. When they found the person, the dogs tore the flesh from their body. When this enslaver died, his last words were that he was going to hell but wished to be buried with his money.

Another neighbor, Mrs. Wade, loved to whip her workers.

A boy named James—the son of “a valuable slave, named Charity” (79)—was sold to a wealthy enslaver known for his cruelty. After receiving a particularly severe whipping, James escaped to the woods. He was captured weeks later and given hundreds of lashes. He was then secured between the screws of a cotton gin and left there for as long as he had been in the woods. Every morning, another enslaved person delivered bread and water to James. One morning, the worker, who was forbidden to speak to James, complained of a stench emanating from the gin house. When the overseer unscrewed the gin, he found James’s dead body, “partly eaten by rats and vermin” (80).

Enslaved women were of “no value, unless they continually [increased] their owner’s stock” (80). The plantation owner who kept James had once shot through the head an enslaved woman who had sought freedom.

Jacobs considers the question of whether an enslaver can ever truly be humane. A white woman who had been an orphan inherited a woman and her six children whose father was a free man. When it was time for the enslaver to marry, she offered to free her workers, knowing that her marriage might change their relatively comfortable situation. They insisted on remaining with her. When the new husband claimed the children as his property, their father was furious. The white woman succeeded in obtaining freedom for the man’s wife but claimed she could do nothing for the children. When the father attempted to get his children off the plantation, he was put in jail. The eldest sons were sold to Georgia. One girl, too young to work, was left in the care of her mother. The three others remained with the enslaver. The eldest soon became the mother of a child who was clearly her enslaver’s. The enslaver then sold her and the child to his brother, who had two more children with this young woman before she was again sold. One of the sisters experienced a break with reality. At the end of his life, this enslaver was regarded as a decent one, for he had fed and clothed his workers and seldom whipped them.

An enslaver’s children learned early about “the unclean influences every where [sic] around them” (83). white girls knew that their fathers exercised total authority over the enslaved women in the household. In some instances, the young women exercised similar authority. Harriet recalls a plantation owner shamed when his daughter had her first child and his first grandchild with an enslaved man. Before her father could exact revenge, she freed the enslaved man. In cases such as this, Harriet notes, the baby was either smothered or sent far away.

After Harriet’s lover departed for the North, Dr. Flint devised a new plan. He decided to build a house for her in a secluded area four miles from town. Around this time, Harriet met Mr. Sands, “a white unmarried gentleman” who was fond of her and expressed a wish to aid her in her situation with Dr. Flint (88). Harriet enjoyed having a lover who didn’t have total control over her, but who had gained favor only through affection and attachment. If Harriet had given in to Dr. Flint, she knew that any children they had would be sold. However, any children she had with Mr. Sands would be cared for and eventually freed.

Harriet refused Dr. Flint’s latest offer and revealed that she was pregnant. Mrs. Flint hysterically accused Harriet of having improper relations with her husband. Harriet’s grandmother expressed her shame, unfortunately, believing the same thing. After Harriet told her grandmother the truth, Martha pitied and forgave her.