Inside Oprah Winfrey & Stedman Graham's Relationship Through The Years

When the name Oprah Winfrey comes to mind, you naturally go to her long-running eponymous talk show, or her status as one of the wealthiest women on the planet. But Winfrey is also known for having one of the longest-lasting relationships in Hollywood, with businessman Stedman Graham. Although the couple never married, their close to 40-year relationship has lasted far longer than most Hollywood marriages.

Having kickstarted their romance in 1986, they've largely kept their relationship away from the public eye. At times, however, either Winfrey or Graham have come out of the woodwork to speak on their relationship, and the highs and lows of maintaining such a strong, long-term bond. However, we have no doubt that Winfrey and Graham's relationship is on par with these five celebrity marriages that we think will stand the test of time, which is why we've decided to do a deep dive of how their romance has evolved over the years.

When Oprah Winfrey and Stedman Graham first met back in 1986, she never thought anything would come of it. In fact, Graham wasn't even available at the time, having been romantically linked to someone else after his divorce from ex-wife Glenda Graham. Even after they met again by happenstance, Winfrey revealed that she considered Graham too attractive, and that there must be something off about him as a result. "They figured if he looked like that, he either had to be a jerk or want something," Winfrey shared candidly with People in an exclusive spread back in 1992, per Oprah Daily.

Thankfully, Winfrey's initial assumptions of Graham were wrong. He turned out to be the complete opposite. What's more, the timing was also right for their relationship to turn official since Graham had split from his previous partner. Essentially, the stars aligned for the couple, and it's definitely a decision that Winfrey never regretted.

All relationships go through a rough spot once in a while, but it happened for Oprah Winfrey and Stedman Graham quite early in their relationship. In 1989, the couple were hit with scandalous rumors that Graham had been having an affair with Winfrey's hairdresser behind her back. Ann Gerber, a gossip columnist for the Chicago Sun-Times, spurred the rumors in the first place. However, it ended up being totally unfounded, and Gerber publicly withdrew the story.

It seemed Winfrey kept the faith, and was right on the money about Graham's character. "He's kind and supportive. ... Lots of people want to ride with you in the limo. But you want someone who'll help you catch the bus," Winfrey exclusively told People in 1992, per Oprah Daily. After this bump in the road, there were no more spurious accusations of infidelity flooding the press. The couple's relationship went from strength to strength.

Throughout all the ups and downs of their long-running romance, both Oprah Winfrey and Stedman Graham had given the world small peeks into their relationship and just how supportive they are of one another. Winfrey had been quite public with her weight fluctuations and body image struggles, and she was appreciative of how Graham had always accepted her through it all. "I love Stedman very much," Winfrey shared, per Elle, "And he cares about me and has been very supportive of me, fat and thin."

Graham had also publicly voiced that Winfrey will always find a solid support system in him. "The thing about our relationship is I want the best for her," Graham said during a segment of "The Ellen DeGeneres Show." What's more, Graham added that you can only find contentment within yourself first, and that having someone that complements him as well as Winfrey does just makes life more complete.

In 1993, Stedman Graham got down on one knee and proposed to Oprah Winfrey. While Winfrey accepted, the pair ultimately decided to not walk down the aisle. Although you may think this would be one of the red flags in Oprah and Stedman's relationship we can't ignore, Winfrey had a good reason for it. In fact, it was this self-awareness that likely saved their relationship in the long run.

"I realized I didn't actually want a marriage. I wanted to be asked," Winfrey wrote in an op-ed for Oprah Daily. She then added that her work was too important for her, and that marriage might not be the right path for both of them as a couple. Winfrey was already happy that Graham loved her enough to propose, with Graham himself acceding to Winfrey's wish not to tie the knot. This proves just how much respect they have for each other, and shows just how differently relationships work for different couples.