After leaving home, Ruth moved to New York City to stay with Bubeh, and began working for Aunt Mary in her leather-goods factory. Aunt Mary was an obese, pretty-faced woman with a husband who made shoes for movie stars. Aunt Mary was, however, having an affair with her best friend's husband. In 1939, she hired a man from North Carolina named Andrew McBride, who went by his middle name, "Dennis". Dennis quickly became Aunt Mary's best artisan. At this time, Ruth was just beginning to discover Harlem; it was "like magic". She went to the movies and looked for a job there, too, but no one would hire a nineteen-year-old white girl. Eventually, she found a job as a beautician, but damaged a client's hair and was fired. Finally, she was hired to work in a nail salon. Rocky, the owner of the salon, was in his fifties and drove a nice car, and Ruth thought of him as "prosperous". Before long, he was driving her home, taking her out, and setting her up in a room of her own in Harlem. Ruth would stay away from home for days at a time, and Bubeh started getting suspicious. Ruth, however, wasn't as innocent as she seemed: she knew that Rocky wasn't only a nail salon owner. She had even begun inquiring how she could go out and make money like his other girls. When she ran into Dennis in Harlem, he shamed her, telling her that her family was worried about her and that Rocky was a pimp. Her parents, he said, didn't raise her to become one of Rocky's women. Dennis's disappointment prompted Ruth to move back to Bubeh's. Rocky tried to win her back, but eventually stopped coming around.
In 1974, James and his family moved to Wilmington, Delaware, because they couldn't afford to keep up the house in Queens. James was looking forward to a fresh start, but his younger sisters didn't want to move. After a great deal of debate, the family decided to leave Queens, but arrived in Delaware only to discover that the schools in Wilmington were segregated. When James's older brother David was pulled over for making an illegal U-turn (he was a doctoral student at Columbia at the time), Ruth decided that she hated Delaware. At 54 years of age, Ruth was living off of a small pension and social security, and still had five children to raise. James enrolled with his sisters in the all-black public high school, where he found a new crowd, focused on music, and won the opportunity to go to Europe. The trip wasn't free, but a rich couple, the Dawsons, had donated money so that inner-city kids would be able to take advantage of such opportunities. In exchange, James worked on their estate. When Mrs. Dawson discovered him sleeping in a strawberry patch she fired him, but still paid for his trip to Europe. The Dawsons kept in touch with James even after he left for Oberlin, which he attended for its strong liberal arts program and music conservatory: James vividly recalls receiving a letter from Mrs. Dawson telling him that her husband had died. In September of 1975, he got on a Greyhound bus and watched his mother wave good-bye to him, remembering how she had always rushed her children out the door, telling them to learn to live on their own.
After leaving Rocky, Ruth made a brand-new start. She found work as a waitress in a diner, and began dating Dennis. He was thoughtful and serious; a violinist who originally dreamed of playing with an orchestra. In those days, however, no orchestra would hire a black man. Undaunted, Dennis composed his own religious music, although he nearly starved to death. Finally, he decided to take a job working in the leather factory. Dennis's family welcomed Ruth with open arms, although Aunt Candis, Dennis's favorite, said: "I just hope you excuse me for looking at you so hard, because I've never had a white person in my house before, and I've never been this close to a white person before." Aunt Candis lived to be a hundred, and when Dennis died, she moved to New York to help with the children.
Although Dennis wasn't ready quite ready to wed, he and Ruth lived as husband and wife. One day, she simply left Bubeh's apartment, causing a scandal. Another day, in 1939, Ruth suddenly decided she wanted to talk to Mameh. She called home long-distance, and Tateh answered the phone. He said that Mameh was ill, and that he needed her to come down and to help with the store. When Ruth arrived home, she discovered that her father was having an affair with a fat, white gentile woman who lived up the road. Soon afterwards, Tateh went to Nevada and got a quickie divorce from Mameh. Dee-Dee, Ruth's younger sister, begged Ruth to stay home. According to Ruth, Dee-Dee was very smart and confident, and got good grades. No one ever made fun of her: "she was the first American in my family, while Sam and I were immigrants." Tateh was proud of Dee-Dee, too, which made Ruth a little jealous. The two sisters were not that close, so she knew that Dee-Dee's request carried great weight. Although Ruth promised that she would stay, in the end she broke her promise: something that Dee-Dee never forgave her for.
When Ruth moved to New York, she sought a fresh start away from her family in Suffolk. Although she remained connected to her mother's side of the family by moving in with Bubeh and working for her Aunt Mary, the move was an overt expression of Ruth's desire to determine the direction of her own life.
Ruth's first independent move, however, was a false start. While she was genuinely attracted to life in Harlem, her involvement with Rocky revealed that she wasn't as innocent as she seemed; she was aware that he was a pimp, and understood where the relationship was heading. At the same time, her attraction to Rocky's lifestyle is not wholly surprising, since pimps often lure in new women by dangling the image of the "good life" before them. For the first time, Ruth felt free, and reveled in the excitement of Harlem. She also most likely believed in Rocky's image of "prosperity". The usage of this phrase adds even more depth to her character: in the reader's mind, at least, Ruth was very far from being an innocent "victim".
Dennis was a new and positive influence in Ruth's life: he shamed her out of her relationship with Rocky, and she made another fresh start. She found work as a waitress, moved back in with Bubeh, and began a serious relationship with Dennis. This relationship was something different: Dennis was serious, kind, and good. He was also religious, but his religion was expressed through his morality and warm-hearted nature, and was not expressed as the tyranny she had experienced living under Tateh. He did not expect the kind of confinement her mother had endured in her efforts to live up to the idea of the "good Jewish wife". Dennis was something different, and in the end he offered Ruth the love and affection that had been absent in her childhood.
For James, the "fresh start" happened when Ruth moved the family to Wilmington, Delaware. The move was clearly an echo of her youthful tendency to physically move away from a site of pain. Ruth had lost both of her husbands and found herself in dire financial straits, and the move expressed her need to start over. James understood this, and welcomed the opportunity to make new friends and escape his rebellious past. He began concentrating on his education, building on what he had learned from Chicken Man. He focused on his passion for music, and sought opportunities for development in the musical arena.
James's relationship with the Dawsons shows the complexities inherent in race-based divisions. While on the one hand the Dawsons employed James as a waiter and groundskeeper, traditional jobs that placed him in a "serving" capacity, they simultaneously worked to provide him with a valuable opportunity to further his education. While they eventually fired him for failing to perform his duties, they did not take away the crucial opportunity that they had given him to travel and play with the jazz band in Europe. James highlights his gratitude to this couple and relates to readers that it was difficult for him to categorize them - white, privileged, wealthy - as "the enemy" in the fight for civil rights. He knew them on a personal level; they were human beings to him, not just "white people". James's relationship with the Dawsons thus reinforces Ruth's statement to her children: it doesn't matter what color someone is if they're a nobody. A person's ultimate value, in other words, is not dependent upon the color of their skin.
The memoir also contrasts Aunt Candis and Jacqueline (James's "aunts") with Ruth's aunts (Mameh's sisters). Aunt Candis and Jacqueline offered James their help, love, and guidance, particularly after Dennis's death. They created the sense of a shared responsibility for one another's fates in a way that Ruth's aunts failed to do. While Ruth's aunts had always ensured that she had enough to eat, Ruth had never felt "loved" by them.
When Ruth returned to Suffolk, the family was on the verge of collapse. Sam had gone; Ruth had gone; Mameh was increasingly ill; Tateh was having an affair. Tateh's affair with a gentile woman is ironic, given the fact that he was a rabbi and was vociferously opposed to even stepping foot inside a Protestant church. The affair also echoes Ruth's own relationship with a black man. Both Ruth and Tateh transgressed the boundaries of their religious community in favor of love.