Why Oprah Winfrey Was Warned About Stedman Graham

Oprah Winfrey has been with her partner Stedman Graham for almost four decades. The couple first met at a charity event in 1986 and while they did reportedly get engaged in 1992, they have never made their relationship official in that sense. But it's not like Stedman didn't want to. Back in 2020, in her column for Oprah Daily, the television personality explained why she and Stedman have never walked down the aisle. She put it this way: "In 1993, the moment after I said yes to his proposal, I had doubts. I realized I didn't actually want a marriage. I wanted to be asked. I wanted to know he felt I was worthy of being his missus, but I didn't want the sacrifices, the compromises, the day-in-day-out commitment required to make a marriage work. My life with the show was my priority, and we both knew it."

Yet, there was another reason why Oprah felt the need to pause when it came to Stedman and their future together. Sure, he had all the credentials that a successful woman like Oprah looked for in a man. But Oprah admits that other people in her professional circle raised a number of red flags when it came to Stedman. Here's why.

In her same column for O, The Oprah Magazine, Oprah Winfrey admitted that her producers had their doubts about Stedman Graham, even though he did have a reputation for being a respectable businessman. He's the founder of S. Graham & Associates, an educational marketing firm, and has done dozens of speeches at public schools about the importance of identity. If that weren't enough, he has also written two books: "You Can Make It Happen Every Day" and "Identity: Your Passport to Success." Yet there was still something about Stedman that Oprah just couldn't put her finger on. 

Could it be that he was too handsome? Or maybe too single? "I figured he must be a player. So did all my producers. They warned me not to get involved with that Stedman guy," Oprah explained.

Luckily, Oprah did give Stedman a chance and he's been by her side ever since. The two even managed to overcome the hardships of having to quarantine apart from one another during the height of the COVID-19 lockdown in 2020, as Oprah Daily's Instagram account noted. Now, as far as how Oprah's relationship with Stedman looks today, that's what her fans really want to know.

These days, Stedman Graham likes to keep out of the spotlight and prefers to show his support for Oprah Winfrey on the red carpet. But according to Oprah's best friend, Gayle King, Stedman apparently does not mind whenever she "third wheels" their romantic vacations, as the "CBS This Morning" anchor has apparently been doing so since 1994.

Gayle told Entertainment Tonight, "I'm a proud third wheeler. I make no apologies for that. I got divorced back in 1994 and I've been their third wheel ever since. The good news is that Stedman is always very welcoming, so it never occurs to me when she says, 'We're going to so and so,' I'm like, 'When?' It doesn't occur to me that I'm not invited. But throughout the years, we've gone on some great trips together. And that's not gonna change."

With that said, it truly sounds like Stedman is Oprah's ride or die to the very end, even if her BFF Gayle happens to be in the backseat.