"Jubilee" is about aging and regret. The story concerns a fifty-year-old male prostitute named Mr. Chalfront, who knows his days in his chosen profession are coming to an end due to his being well into middle age. Though he has debonair manners and a handsome face, his methods are becoming dated and labored due to his age ("he made love attractively in his formal, well-bred way, but they'd have outloved him"). Hard times have also made it hard for him to dress attractively, so he is stuck with frayed clothing. While on the lookout for clients, he encounters a successful brothel madame, who takes pity on him and enlists his services so he will not feel bad for taking her money.

All of this happens shortly after George V's Silver Jubilee in 1935, and that event is linked to the theme of the regrets that come with aging. A royal jubilee is a celebration intended to honor milestones in the reign of a monarch. What is ironic is that unlike the king, who is celebrating twenty-five years on the throne, Mr. Chalmont feels he has no similar achievements. He avoids going out during Jubilee so no one he knows will learn how poor he is. He is a man with nothing but regrets: he regrets having no male friends to talk to, in particular. By the end, Mr. Chalmont has fallen about as far as he can go, with a woman enlisting his services only out of pity for his poverty and his pride. The final line, "You couldn't call him anything else now but old Mr. Chalfront," emphasizes this fall as well as the suggestion that Chalfront can no longer pretend to be younger or better off than he is.