Aging brings distinctive discoveries and challenges, as well as difficulties. People age in many different ways, but we can learn from shared experiences and insights. Instead of thinking about this stage of life as a time to wilt, we need to think boldly and carefully about the active living that we can do for an increasing number of years. The conversations, or paired essays, in this book juxtapose a philosopher's approach with that of a lawyer-economist. There are ideas about when to retire, how to refashion social security to help the elderly poor, how to learn from King Lear - who failed to retire successfully, and whether to enjoy or criticize anti-aging cosmetic procedures. Some questions are very general: What is friendship as we age? What becomes of love and sex? What goals should a decent public policy have toward aging citizens? Some of the ideas are more immediately practical; the essays deal with philanthropic decisions, relations with one's children and grandchildren, the purchase of annuities, and how to provide for care in old age. And some of the ideas are just interesting; they include the treatment of aging women in a Strauss opera and in many films, as well as some consideration of Donald Trump's marriages to much younger women. The overall goal is to show how much fun discussion about aging can be and, in the end, how to age thoughtfully and encourage one's parents and friends to do so as well.