Oprah Winfrey & Stedman Graham, Together for  33 Years

Oprah Winfrey and Stedman Graham seem to be enjoying life without marriage. They met in 1986 and they were engaged in 1992. However, since then, they’ve continued dating without any news about when they plan to exchange vows. Winfrey has shared that their relationship isn’t exactly traditional and that’s why she’s reluctant to go to the altar.

As of 2019, Oprah has an estimated net worth of $2.6 billion while Stedman is worth an estimated $10 million. Finances often strain marriages and perhaps could be the reason they chose to maintain a “spiritual union” rather than walk down the aisle.