Her former beau thing is Roger Ebert (of the Old School movie critique duo, Siskel and Ebert)!
Can you believe that? Roger is a far cry from Stedman Graham, but guess what? Oprah’s not a far cry from the woman Roger later married and remained married to until his last breath.His wife is Attorney Charlie “Chaz” Hammelsmith. She and Oprah are quite similar from a physical standpoint, so I guess it’s safe to say that Oprah was Roger’s type for sure.

Oprah and Roger both confirmed that they briefly dated back in the day, although they only officially went on two dates. One of those dates turned out to be extremely lucrative for Oprah because it was Roger who convinced her to allow her show to go into syndication. When he shot some profitable numbers out at Oprah, she said she was sold. Here is a snippet of what was explained about that particular date on Oprah.com:
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Oprah may remember her first date with Roger more clearly because it’s the one that really paid off!

Naturally, Roger took Oprah to a movie on their first date, and then he treated her to dinner at the Hamburger Hamlet. Over dinner, Oprah told Roger that both King World and the ABC stations wanted to syndicate her local talk show, but she wasn’t sure what to do.Roger grabbed a Hamburger Hamlet napkin and started jotting down some numbers. First, he took his annual salary multiplied by two (because his co-critic at the time, Gene Siskel, made the same salary). Then, he multiplied that number by five since Oprah’s show would be on five days a week. Finally, he doubled that number to reflect the hour timeframe, and then doubled it one last time because he was sure her show would be a huge hit!

He slid the napkin across the table to show Oprah the final tally and she said, “Deal done!”

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Oprah.com

Both of them moved on to long term relationships. Oprah with Stedman, and Roger Ebert married his wife.
Although Ebert married, Oprah made it clear two years ago that she would never marry Stedman and here’s why:
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“He [Stedman] would tell you that had we married, we would not be together today, because he’s a traditional man and this is a very untraditional relationship.”
“I think it’s acceptable as a relationship, but if I had the title ‘wife,’ I think there would be other expectations for what a wife is and what a wife does. First of all, you’ve got to come home sometimes,” Oprah laughed.

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NYPost

Ebert married his wife at the age of 50 because he said that he couldn’t dare get married while his mother was still living out of fear he would “disappoint her.” I’m not sure where the disappointment would have come from, because his wife seems like a successful, intelligent woman, so the most obvious reason I could gather would be that maybe he was worried his mom wouldn’t approve of their racial differences. I could be 1000% wrong on that, but that’s the biggest difference from the outside looking in. Anyways, it’s great seeing Ebert and his wife being able to find true love, regardless of what others may have felt about their relationship.

Roger Ebert sadly passed away at the age of 70 on April 4, 2013 after an 11 year battle with cancer. He is survived by his wife. May he continue to rest peacefully.

-ILoveOldschoolMusic, Old School news with a new point of view