Drawing from over 11,000 comments across Reddit, YouTube, and Facebook, this report explores how Americans are redefining the "ideal age" for key life milestones—marriage, parenthood, homeownership, and retirement. While many align on the late 20s to early 30s as a preferred window for marriage and starting a family, financial readiness and emotional maturity are seen as more important than any fixed timeline. Comments reveal growing skepticism toward traditional expectations, with many highlighting rising costs, economic instability, and shifting cultural values as major barriers to hitting these milestones “on time.” Retirement is increasingly viewed as a privilege tied to wealth, not age, and homeownership is often described as aspirational but increasingly out of reach. Rather than following a standard script, Americans are negotiating deeply personal timelines shaped by practicality, resilience, and evolving definitions of success. This analysis surfaces how public sentiment is moving away from societal pressure and toward self-determined paths.