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We all age differently, but we can learn from shared experiences and insights. The conversations, or paired essays, in Aging Thoughtfully combine a philosopher's approach with a lawyer-economist's. Here are ideas about when to retire, how to refashion social security to help the elderly poor, how to learn from King Lear -- who did not retire successfully -- and whether to enjoy or criticize anti-aging cosmetic procedures. Some of the concerns are practical: philanthropic decisions, relations with one's children and grandchildren, the purchase of annuities, and how to provide for care in old age. Other topics are cultural, ranging from the treatment of aging women in a Strauss opera and various popular films, to a consideration of Donald Trump's (and other men's) marriages to much younger women. These engaging, thoughtful, and often humorous exchanges show how stimulating discussions about our inevitable aging can be, and offer valuable insight into how we all might age more thoughtfully, and with zest and friendship.