Every Sunday, the Deads pile into Macon's plush green Packard for a ride about town, mostly to convince Macon himself that he was indeed a successful man. One particular Sunday, as the family was driving up to Honore Lake because Macon was debating on investing in beach houses, Milkman decided that he could no longer wait to use the bathroom. As the car halted to a stop on the side of the street, Lena accompanied Milkman into the woods so that he could relieve himself. While he was doing so, Lena wandered around picking flowers and then headed back by Milkman. Hearing her approaching footsteps, Milkman turned around while still in the act of urinating, and wet Lena's dress. Milkman's habit of constantly turning around and looking back indicates to him that there was no future to look forward to.
However, although there may have been no future in sight, life progressed and at the age of twelve, Milkman had befriended Guitar, a mature high-schooler, and met his aunt Pilate. Their relationship began one day when the two boys purposely came across Pilate, dressed in all black, sitting on the front steps of her home peeling an orange. After a preliminary introduction in which Milkman screamingly defends his name when Pilate says there are only three Deads alive, the boys are eager to get inside Pilate's wine house. Accepting Pilate's offer of soft-boiled eggs, they follow the tall, skinny, unkempt woman into a large sunny space where the odor of fermenting fruit permeates the air.
With the wine smell making both boys drowsy, Pilate is free to talk continuously about her childhood experiences. Pilate talks about the gratitude she feels for Macon for saving her life twice, once during her birth and once again in the dark woods. She talks about her father being blown five feet into the air while sitting on a fence on his own farm in Montour County, Pennsylvania. And, after her father's death, she claims that she and Macon saw his ghost sitting atop a stump in the forest, an experience that left that them shaking like leaves.
As Pilate talks on, the mellow scene is interrupted when Reba and Hagar arrive home struggling with five-bushel baskets of what looked like brambles. Milkman instantly falls in love with Hagar, prior to even seeing her face. He is introduced to Hagar as her brother, as Pilate states one should act the same towards cousins as towards brothers. As the night progresses, the women tell stories while mashing berries for the wine. They laugh about Reba's luck of winning a diamond ring at Sears' for being the 500,000th customer, when she only walked into the store to use a washroom. In fact, Reba's luckiness is a source of pride to her, having won everything from one hundred pounds of free groceries to diamonds, she claims now no one will sell her a raffle ticket lest she win. The easy-going conversation turns morose as Hagar says she has been hungry, but not in respects to food. The night ends with Pilate, Reba and Hagar singing away in perfect harmony, "Oh Sugarman done fly away..."
Milkman's practically perfect day ended when he arrived home to find his father waiting for him. Freddie had told Macon about Milkman's whereabouts and the two engage in a verbal argument resulting from an emotional power struggle. Milkman ends the argument by beginning a discussion with Macon on how he felt about his father when he himself was twelve. With that, Macon tells the tale of his childhood days of working alongside his father, and the farm he lived on, which boasted a fortune in trees, a stream full of fish, a big barn with a four-stall hog pen, and a four acre pond. He reminisces about a cherry pie Pilate tried to make for him from the farm's own fruit trees. Macon also elaborates on how his father lost his farm, blaming the man's illiteracy for every negative thing that happened to him in his life. It turns out that Macon Dead I had signed a piece of paper which officially signed his property over to a white family. And, as Pilate previously recalls, he died sitting on his fence trying to keep possession of his property. Also, the reason for the clerical mistake behind the accidental Dead family name switch occurred because his father could not read to correct the wrongly entered information. When Milkman inquires about his grandfather's first name, Macon instead comments on how his mother was light-skinned and pretty.
The father and son conversation draws to a close when Macon once again reaffirms his negative feelings about Pilate. Macon claims she does not look normal and that she is a snake ready to cut throats. As his father tells him he is banned from associating with Pilate, Milkman asks questions in hopes of understanding why his father claims that she is a snake. Macon's response indicates that although he thinks Pilate can teach Milkman something in the next life, she is useless in this one. As for Milkman's own productivity, Macon informs him that starting Monday Milkman will be learning the real estate business.
Even as a young boy, Milkman wariness towards the future is reflected in his actions. The narrator informs us that he is constantly turning around in order to see what is behind him. Such behavior indicates that he is aware, if only subconsciously, of the lack of future in front of him. Such behavior also emphasizes the importance of having a past, and generally relates to the concept of identity.
As previously mentioned, Macon Dead II has an unsettling desire to accumulate wealth. This love for material possessions was instigated through watching his father die trying to defend his property. As a result, Macon Dead II has rejected natural loves of humanity, instead preferring wealth and power to a happy, spiritual existence. Milkman has inherited his father's lack of spirituality, and appears to be heading down the same path of destruction. And yet, some glimmerings of hope are visible because even as a child Milkman inquires about his family history, specifically about his grandfather's name. Milkman's interest in his identity suggests that he may choose a different path from his father after all.
While many of the characters are emotionally, and perhaps physically, trapped within their own circumstances, Pilate appears to be the only one is liberated. She carries a secret knowledge within her, suggesting she is in control of her destiny and identity. Ironically, just as Macon is well-dressed with a contaminated character, Pilate is unkempt from the outside but clean and pure on the inside. She rejects any desire for material possessions, and is sure of her ground in this world. It is Pilate who, in the last chapter, inspires emotion in the typically cold Macon Dead II. She also inspires a quest of identity in Milkman, who only after visiting her begins inquiring about his family's past.
Both Pilate and Macon Dead II discuss growing up on their father's farm, yet their accounts somewhat differ due to omission. Milkman's father does not recount his experience in coming across his father's ghost while Pilate stresses this event. She claims that it scared her, and her openness in discussing the event shows that she is aware of the fact that she is still haunted, emotionally and spiritually, by her father's death. In admitting that she is haunted, Pilate understands that there is a family problem extending from generation to generation. Macon Dead II's omission of the accident may be interpreted on different levels. Perhaps he purposely did not discuss the accident or else he may have simply forgotten. In either sense, he clearly does not want to be reminded of the spiritual problem he is facing, or he may be completely unaware of it.