OPRAH WINFREY AND STEDMAN GRAHAM – 32 YEARS


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Just before The Oprah Winfrey Show premiered in 1986, talkshow queen Oprah met a tall educator by the name of Stedman Graham, at some charity function in Chicago, where he was there representing his own nonprofit organization called Athletes Against Drugs. And although people warned her that the handsome divorcé may be a jerk, she took her chance and went out with him. Six years later, he gave her a diamond ring.

Stedman and Oprah eventually ended their engagement but there were no family lawyers or attorneys involved, since the couple never got married or had kids together. They both still lived together, and have been together since, even becoming grandparents in 2015 as Wendy, Stedman’s daughter from a previous marriage, who is very close to Oprah, delivered her first child.

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