Oprah Winfrey,  Age 65 – In a Relationship

Since the very first season of The Oprah Winfrey Show, Oprah and Stedman Graham have been sharing their lives. However, even though they announced their engagement back in 1992, they never actually went through with the wedding. More than three decades have gone by, and they’ve never actually tied the knot.

The reason behind it is actually fairly simple. According to them, if they were to get married, they would slip into this traditional way of being, which, clearly, they find not fitting for them. Oprah might have finished her show, but Stedman just released a new book in 2019 titled Identity Leadership: To Lead Others, You Must First Lead Yourself.