Oprah Winfrey Waited 6 Years for Fiancé to Propose — She Has Been Engaged for Nearly 30 Years

Oprah Winfrey was warned against dating a boy she met in 1986, but she went on to fall deeply in love with him, and after some years, he proposed, sparking speculations of a marriage that never happened — this is their story.

It is worth noting that Stedman had fine features as a younger man. Such a good-looking guy focusing all that attention on one woman that did not feel like she deserved it rubbed Winfrey’s staffers off wrongly.

It had something to do with how they knew next to nothing besides the fact that he drove a vintage Mercedes and looked very good. “Don’t get involved with that Stedman guy,” they told her, and she listened. She once admitted:

“They figured if he looked like that, he either had to be a [expletive] or want something.”


View this post on Instagram


A post shared by Oprah (@oprah)

She decided to take things slow even as his friend until she discovered months later that he had broken up with his lover and had been asking around about her status. It was what made Oprah, ever the pragmatic one, consider him seriously, and it was the beginning of their story.


When Oprah and Stedman started dating, many rumors about them appeared in the papers. They had been dating for years, and it did not seem like anything would change, so there was a lot of speculation on when the wedding bells would ring.

Oprah Winfrey and Stedman Graham during The 19th Annual Daytime Emmy Awards at Sheraton Hotel | Source: Getty Images

When the whole affair started getting out of hand, Oprah confessed that she was the one not rushing the marriage plans. Apparently, it gave her a sense of freedom, and she also refused to wear any type of ring — not even the engagement ring.

Stedman also seemed to be on the same page with her because he was “marriage shy” after having been married once before meeting Oprah. He was a divorcee who wanted nothing more than to avoid repeating past mistakes.


View this post on Instagram


A post shared by Oprah (@oprah)

The relationship progressed nicely, and Oprah fell deeper in love so that at some point, she would prefer to sleep in her office than at home while he was away.

However, despite the apparent love welling between the two of them, they did not get married, and they respected boundaries.

Years passed before Oprah admitted that Stedman now “keeps a toothbrush at my apartment.” It was a step in the right direction as far as the fans were concerned, but it did not guarantee marriage, as they would soon find out.

Stedman Graham and Oprah Winfrey arrive on the red carpet for the premiere of  "The Butler" on August 5, 2013 | Source: Getty Images


Stedman blindsided Oprah with a wedding proposal because she didn’t even know something like that would happen. One afternoon in October, she was hanging out with her friend, Gayle King, while waiting for her partner, who doubled as her public relations man.

According to oprah, doubt started flooding in after she said yes to his proposal.
Stedman was to arrive from Chicago with a tape of Oprah’s upcoming show. When he arrived, she went outside to meet him, and by the time she returned to the kitchen, something was different: Stedman had popped the big question.

Author, businessman, and ex-athlete Stedman Graham hugs his girlfriend, talk show host Oprah Winfrey at Radio City Music Hall | Source: Getty Images

“You are not going to believe this. Stedman just proposed!” she exclaimed to her friend, King, who was just as stunned as Oprah was.



Related Posts

Leave a Reply

Your email address will not be published. Required fields are marked *