Bombarded with youthful images in both gay and mainstream media, many gay men approach midlife with a sense of foreboding. Are You Ready counters common stereotypes about aging in the gay community. In lively discussions with ten gay men, it describes positive aspects of midlife, and how to deal more effectively with the changes (and challenges) that commonly take place at this time of life. Some of the topics include physical and sexual changes; loss and mortality; impact of midlife on gay relationships; and dating at midlife. Authenticity, generativity, equanimity, and a sense of meaning are some of the positive aspects many of the men discovered as they entered this phase of life. The last chapter compares gay men at midlife with the “trickster” figure in traditional cultures, and shows how many gay men meet midlife challenges with wisdom, healing, and humor.