Aging brings special experiences and challenges, but also problems. When is the right time to retire? Should one reject anti-aging products, or are they welcome tools for aging on one's own terms? Why do some powerful men seem so fixated on younger women? Philosopher Martha Nussbaum and legal scholar and economist Saul Levmore explore these topics in their respective essays, which come together in a conversation. They reflect on literary figures like King Lear, analyze popular films, and share their own experiences with aging. A humorous, insightful, and enriching dialogue unfolds between two friends, demonstrating that it is worthwhile to approach this stage of life consciously and thoughtfully.