What Oprah Winfrey's Exes Have Said About Her

Oprah Winfrey has been in a relationship with Stedman Graham for almost as long as she has been famous. The talk show queen began dating the handsome businessman in the mid-1980s, despite initial reservations. "I thought he was nice enough, but I wasn't that impressed," Winfrey wrote of Graham in her Oprah magazine column in 2020. "He was polite, yes, and kind... Tall and handsome, for sure. But actually too handsome, I thought, to be interested in me. I figured he must be a player." Winfrey added that even her show producers warned her against getting involved with Graham.

She ignored her instincts, as well as producers' advice, and four decades later, Winfrey's romance with Graham is still going strong. While the two never married, Graham told "The Ellen DeGeneres Show" the reason the relationship works is because he and Winfrey want the best for each other. "I'm dedicated to her happiness," he said. "And I want her to be the best she could possibly be... And so, for me, I've been able to find my own happiness, and to find my own skills, my own talents, and my own abilities. And I'm satisfied with that. And so, the combination — when you have a good partner that's able to self-actualize their potential, and you're able to self-actualize yours — then one and one equals about six."

But Winfrey had other romances before finding her life partner in Graham, and a few of them were even celebrities like her.

Oprah Winfrey's high school sweetheart said she wanted to be a movie star

Oprah Winfrey's first serious boyfriend was Anthony Otey. The two dated in high school, going official on September 22, 1970, and even talked of marriage, per The Sun. But Winfrey broke up with Otey during their senior year at their Nashville high school. 20 years later, she reunited with him on "The Oprah Winfrey Show."

During their reunion, Otey recalled first meeting Winfrey at a community center dance. "She was a very bright, very articulate person," he said of the future media mogul. On her end, Winfrey admitted her father was wary of Otey because he had dated a rival schoolmate before courting her. Once they did get together, the teen lovebirds exchanged "mushy" notes and sweet mementos. For his visit to Winfrey's studio, Otey even brought a memory book he'd held onto since high school. "One thing I remember most... is that she knew what she wanted very early in life," he said of Winfrey. "She said she wanted to be a movie star. She wanted to be an actress. And I praise God that she's done that."

Oprah's ex, Bubba Taylor, did not want to get married

In the early 1970s, Oprah Winfrey began dating William "Bubba" Taylor after meeting him at Tennessee State University. The relationship ended in 1976, when Winfrey moved to Baltimore for a TV news job, per The Sun. In 2020, Winfrey wrote about Taylor in her Oprah Magazine column, where she revealed that he neglected to send her flowers when she competed as Miss Black Tennessee in a beauty pageant. "Many of the other girls were receiving flowers and gifts from their beaux. My boyfriend at the time, Bubba — yes, real name — sent me nothing," she wrote.  

Winfrey's relationship with Taylor was also complicated by the fact that her dad, Vernon, did not like him. It also didn't help that Taylor did not want to get married. In 2012, Taylor described his relationship with Winfrey as serious in an interview with The National Enquirer. "I knew Oprah wanted to get married, but she also knew I didn't want to talk about marriage. I was only 27 years old and getting married was not on my mind," he told the outlet. 

Taylor also shared that he always knew Winfrey would go on to do great things. "When it came time for her to move to Baltimore, I drove her there and helped her unpack," he said. "But we both agreed I would not make the move with her because I was in my family business, and she needed to be in a bigger television market."

John Tesh said Oprah had an amazing sense of humor

Before she moved to Baltimore, Oprah Winfrey also dated future "Entertainment Tonight" host John Tesh. According to Us Weekly, in 2010, Tesh spoke of the romance, saying, "Oprah and I were cub reporters in Nashville nearly 40 years ago and we dated for a short time. We even talked about it during one of my appearances on her show."

Tesh elaborated in an interview with journalist Michael P. Coleman, where he revealed that Winfrey was 19 and he was 21 when they worked at rival Tennessee news stations. In the interview, Tesh noted that he and Winfrey would compete to cover similar stories, such as local fires or city hall news, but that they always looked out for one another. "We would go out to lunch and go to movies together, and we'd have dinner," he said. 

Tesh also revealed that when they went out in public together, some people took issue with the fact that they were a biracial couple. "It was 1974, and we would go to a restaurant and people would leave the restaurant because it was a white guy and a black woman," Tesh said. "And of course, Oprah had the most amazing sense of humor. She would say, 'Hey, what restaurant are we going to empty today?' And I'd say, 'Hey, yeah, let's clear out a restaurant!'"

Despite their relationship ending, Tesh also confirmed that he remains friends with Winfrey, even to this day.

Roger Ebert gave Oprah Winfrey career advice

Right before she shot to superstardom, Oprah Winfrey went out with a movie critic who would give her the biggest advice of her life. It was the mid-1980s and Winfrey went on several dates with Roger Ebert, the second half of the famous Siskel and Evert movie critic duo. In a post on his website, Ebert recalled first meeting Winfrey when she hosted a local Baltimore talk show. He later reconnected with her when she was hired to host "AM Chicago." "At about this time, Oprah and I went out on a date," Ebert wrote. "Well, actually two dates, but the one that made history began when we went to the movies. Afterward, we went to the Hamburger Hamlet for dinner, my treat."

Ebert said he advised Winfrey to syndicate her morning show after she told him she didn't know what to do with offers that had been presented to her from ABC and King World. "I took a napkin and a ballpoint pen, and made some simple calculations," he recalled. "I pushed the napkin across the table. Oprah studied it for 10 seconds. "Rog, I'm going with King World,' she said.'"