Oprah and Stedman

No Ordinary Love

Rumor has it that Oprah Winfrey’s ex-boyfriendReginald Chevalier is still bent out of shape over their relationship that ended years ago. He claims that Oprah only dumped him in 1985, because she started seeing her longtime boyfriend Stedman Graham. Reginald might want to start letting it go. For the last 25 years Oprah has been connected to Stedman and for the last 25 years the public can’t seem to get enough of their tight lipped relationship. In the last year, Oprah has opened about this part of her life, proving that long-term couples can be happy living non-traditionally, without marriage and children. See how it works for them…


Oprah Winfrey and Stedman Graham began dating back in 1986, after Graham’a failed marriage and and Oprah’s failed relationship and scandal with ex-boyfriend Randolph Cook.

I Got Your Back

Oprah went through a depressing time in the 80s when someone sold her out to the tabloids for $20,000. When Stedman showed he was truly there for her, she knew she loved him. “Here is someone who is willing to stand in and stand up for you. And that is love,” she said.


New Jersey native Stedman — standing at 6’6 — was not only a college basketball star, but at one point a successful sportswear model. Graham is currently the CEO of S. Graham & Associates, a Chicago-based corporate and educational marketing and consulting firm.

You Fancy

In the beginning of their courtship Oprah Winfrey and Stedman Graham were always spotted out and about. The two look glamorous at an award gala at the Waldorf Astoria Hotel in NYC in 1987.

Yea I’m With Him

In the 80s Stedman was the epitome of handsome. Oprah recalls him being so good looking that her staffers questioned his intentions. “They figured if he looked like that, he either had to be a jerk or want something.”

My Rock

Graham and Winfrey were engaged in 1992 to be married September 1993, but later canceled, deciding that they would rather have a “spiritual union.”

Just Me and My Man

Oprah says she has no regrets whatsoever about never having children, “I never had a desire. And I don’t think I could have this life and have children. I do feel like I am a mother in a broader sense, to a generation of viewers who’ve grown up with me.”

A Real Man

Stedman has said, “[I’m a] man in a relationship with a very powerful woman. I’m not threatened by her fame, her success, her money; that’s who she is. It has nothing to do with how I define myself.”

Just Kicking It

Oprah admits that her relationship with Stedman is quite normal. Here the talk show host and her boo walk their dogs at a park near Winfrey’s home in Downtown Chicago.

Give Me A Kiss

Marriage or no marriage, Oprah Winfrey and Stedman have been going strong for 26 years.

Stuck Like Glue

Back in 2008 rumors started to swirl that Oprah and her Steddy called it quits. Oprah went on record in 2010 and said that rumor was the furthest thing from the truth, and they still are going strong.

Believe It or Not

In 25 years on the air, Oprah says Stedman has only attended three shows-including one of the annual “Favorite Things” finale.

Support System

In an interview with Barbara Walters in 2010, Oprah went on record saying “I do not know another man on this planet who could have lived this life with such dignity, such grace, and such respect and humility in it, and still hold his own and be his own.”

Love Birds

“I think people are fascinated with the relationship because you haven’t seen him. People want to know what is it? Is it real? What is it really like? What are they really like together? And when you see it, it’s quite normal,” Oprah says.

Don’t Get It Twisted

In that same exclusiveinterview with Barbara Walters in 2010, Oprah declare Stedman is still “the love, the lover, the man, the partner, the mate” of her life.

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