Michael Dean: Oprah introduced Gayle to the TV producer, now 44, in Oct. 2007. He was in her studio audience, Gayle was on the phone, and the two caught comic Chris Rock’s show in Las Vegas the next month. But Chris roasted Gayle from the stage for bringing a much younger date, and the romance fizzled.
Sen. Cory Booker: The New Jersey politician, 46, and Gayle share a bond – they’re targets of gay rumors. He said in 2013: “She’s been an incredible friend.”
50 Cent: Gayle flirted with the rapper, 40, after meeting him at a charity benefit in 2011. But he twice publicly ripped into Oprah, and the friendship infuriated the TV titan.
