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"It's no big deal to have a brother who is homosexual, but apparently it was to Oprah.Tim also said he knew about some lesbian affairs." As for Winfrey's very public relationship with Graham, the pair do not even share a bedroom, according to the book. She did reportedly have one affair with a man -- "Entertainment Tonight's" John Tesh, while the two were working in Nashville.• Oprah Winfrey began dating Stedman Graham in 1986, the same year her namesake show launched.• Winfrey and Graham got engaged in 1992, but ultimately decided against marriage.At one point, the rumors included seamy talk at ABC about a relationship between Winfrey and Sawyer when Oprah worked there.Employees there described "giggly late-night phone calls" and a series of lavish gifts from Winfrey -- including gigantic sprays of orchids and a 1-carat diamond toe ring -- to Sawyer.
And her longtime partner Stedman Graham's comments to the The Los Angeles Times also helped fuel widespread interest in her political prospects.* She went to great lengths to conceal her "lesbian affairs" -- including hefty payoffs -- and publicly attached herself to Graham to appear more normal to her audience of housewives.* She lavished romantic gifts -- including a diamond toe ring -- on ABC talking head Diane Sawyer.• Graham's suggestion that Winfrey run for president at the 2018 Golden Globes isn't the first time he's encouraged her to enter the realm of politics.Interest in media mogul Oprah Winfrey's hypothetical 2020 presidential run is surging. While Trump asserted he'd beat Winfrey, in past years he said the former queen of daytime talk would be his ideal running mate, Business Insider reported.