Oprah Winfrey & Stedman Graham – 33 years

Oprah Winfrey is one of the most influential women in the world. But her long-term relationship with entrepreneur Stedman Graham has been kept deliberately low-key. Since the first time meet at a charity event, he has become a pivotal man in Winfrey’s life for more than 30 years.Dating since 1986, Oprah Winfrey & Stedman Graham announced their engagement in 1992 but never got married.Oprah made it clear that she doesn’t feel the need to exchange marital vows soon. Unlike other couples, these two have a different mindset on marriage.

The iconic TV presenter stated in a column in the February issue of O magazine “Oprah” that if she married Graham, their relationship might never be resolved. Oprah shared that Graham had a traditional expectation of husband and wife, which she believes is a role that wouldn’t fit her, to the degree that they might end up going separate ways if they pursued marriage. That’s how they decided not to go through with it. Oprah recently had a voice role for Crow: The Legend in 2018.