Clyde becomes more familiar with the other bellhops and they help Clyde become more familiar with the “entertainments” that are available from connections made at the hotel. Clyde is intrigued by the men who hang around the hotel expecting to earn a reputation as "a man about town." The other boys warn him of men who prey on the bellhops for homosexual relationships. Some of the boys “fall for it,” Clyde is told. Most of the bellhops are from other places and come from broken homes, sometimes with widowed mothers to take care of. All agree that Kansas City is the best place they have visited, and that Mr. Squires is the best boss. The Green-Davidson Hotel is the most luxurious one in town, and the boys feel privileged to be connected with it.

Clyde wonders how to keep most of the money he makes. It is understood by his parents that Clyde should contribute three-fourths of his income to help out the family. Clyde, however, tells them that he usually earns only a dollar in tips, instead of the five or six dollars a night that he actually gets. They feel badly that Clyde has to work so hard and such long hours for so little money, but Clyde assures them that he does not work too hard, and this position will open up to something better.

The boys tell Clyde that one of their nights out is coming up, where they can visit bars, dance halls, and even brothels. They invite him to come along, and though Clyde is initially disgusted by the thought of their sordid activities, his interest in sex overcomes any hesitation; he agrees to join them. He buys some new clothes, which raises some suspicion in the minds of his parents, but Clyde tells them that this is nothing compared to what the other boys wear. He assures them that he is not spending too much money and guarantees them future pay as long as he keeps his job at the hotel. On a Friday night, the boys go to a bar and order drinks. Clyde, never having had alcoholic before, follows the other boys’ lead. After several hours, the boys head to a local brothel. Clyde is nervous, not sure that he should even be there, nor if he can do anything once the occasion arises. He is overwhelmed at the thought that the mystery of sex will be resolved for him, and he waits patiently for the prostitutes to arrive.