Chapter 5 Summary and Analysis

In 1965, Henry is twenty-two and enjoying the high life afforded by his hustling and scheming. He considers himself a good earner, and works harder at his illicit schemes than many people do at honest jobs. Like many young men, however, Henry throws away his money. He tips heavily and gambles away the rest, then borrows money from his friends until his next scheme pays off. He has no social security number, pays no bills, and has no dependents. He sleeps at friends' houses or in "comped" motel rooms and keeps his clothes at his parents' house. He womanizes with prostitutes and neighborhood girls and enjoys his freedom. Then he meets Karen.

Henry gets stuck on a double date with Karen because Paulie Jr. wants to date her friend, Diane. Henry has to meet Tuddy for a deal later that same night...