Oprah's Stepmom Once Dissed Her Relationship With Stedman Graham

There are two unwritten rules in Oprah Winfrey land: Don't come between her and her man, and don't come between her and her bestie. Oprah's stepmom broke both when she dissed her relationship with Stedman Graham and questioned her friendship with Gayle King. 

Oprah's unconventional relationship with Stedman has been the subject of tabloid fodder forever. Per People, the two started dating in 1986, the same year the talk show titan's titular daytime show debuted. Stedman was previously married to Glenda Graham, with whom he shares a daughter, Wendy Graham, and their divorce left him relationship wary. However, after Stedman "swept her off her feet," Oprah played the long game, keeping it cool and eventually bagging her man.

Anyone that dates Oprah has to get used to living in her shadow, something the suave and confident Stedman is happy to do. "He knows that most people see him as Oprah's boyfriend," his business partner told People. "But it doesn't bother him anymore." Oprah and Stedman agree that mutual respect and support are crucial to their relationship. "We want each other to succeed," he said in a rare interview. "And I want her to succeed and to be as successful as she possibly can." But he's happy to play a back seat to the formidable O. "Stedman's only been to three of my shows," Oprah admitted. "So for Stedman to come by a show, extraordinary things must be happening." So, why did Oprah's stepmom once diss her relationship with Stedman Graham?

There's no doubt there are some strange things about Oprah and Stedman Graham's relationship. One of the things people focus on is that Oprah appears to spend more time with her bestie Gayle King than with Graham. That's certainly an issue her stepmom fixated on. Barbara Winfrey was married to Oprah's father, Vernon Winfrey, for eleven years. She let rip to the Daily Mail in a bitter, no-holds-barred tell-all interview.

"Once you're in Oprah's world, she owns you," Barbara vented. She claimed that in the 14 years she was with Vernon, she never saw Oprah and Graham display any signs of intimacy, such as hand-holding or kissing. Barbara alleged that Oprah admitted to having Graham followed by a P.I. and that she only liked him because he had "high yellow" skin and soft hair. Barbara claimed Oprah was closer to King, who was a constant presence. "If it's not more than friendship, they're giving every appearance that it is," Barbara said of the two women.

Well, Oprah would beg to differ. She claimed during an interview with "Hoda & Jenna & Friends" (via Oprah Daily) that she had "manifested" Graham into her life and that following a bunch of failed relationships, he was the perfect partner. "I'd been through a lot of 'woof woofs.' You get to the point when you say, 'No more.' I actually said, 'This is what I want. Someone who is kind. Someone who is loyal.' And that's what I have," Oprah shared.

Another thing about Oprah Winfrey and Stedman Graham that gets detractors worked up is that Oprah rarely vacations alone with Stedman. In fact, on the rare occasions they do take a break, Gayle King is along for the ride. During "The OG Chronicles" (via Oprah Daily), Oprah shared that King has been on every vacation since she got divorced in 1993. "If I was the third wheel, I didn't know it!" King said. "If Stedman didn't like me, that would've been tough."

"If Stedman didn't like you, Stedman wouldn't have lasted," Oprah agreed. "Husbands and boyfriends come and go. Best friends last forever." The unexpected origin of Oprah and King's friendship was finally revealed in 2022. The two told People that they started setting #FriendshipGoals when Oprah was a 22-year-old news anchor, and King was a 21-year-old PA and writer. After a heavy snowstorm rolled in, Oprah offered King a place to crash, and the rest is history. "We ended up talking all night long," Oprah said. "We've literally been friends ever since."

As for the too-close-to-be-just-friends speculation? "I understand why people think we're gay," Oprah admitted in O Magazine (via Oprah). "There isn't a definition in our culture for this kind of bond between women. So I get why people have to label it — how can you be this close without it being sexual? How else can you explain a level of intimacy where someone always loves you, always respects you, admires you?"