Oprah Winfrey & and Her Experiences with Dating.

Winfrey once dated movie critic Roger Ebert, whom she credits with advising her to take her show into syndication. The relationship of Winfrey and Graham has been documented through the years with numerous romantic tabloid articles often accompanied by color spreads of the couple at home and on lavish vacations. Prior to meeting Graham, Winfrey's love life was a lot less stable. A self-described promiscuous teen who was a victim of rape at age 9, Winfrey gave birth at the age of 14, to a boy who died shortly after. In 1997 a former boyfriend named Randoph Cook tried to sue Winfrey for $20 million for allegedly blocking a tell-all book where he claimed they lived together for several months in 1985 and did drugs. Cook's claims mark the second time reports surfaced about Winfrey's involvement in a drug related love affair. In 1995 Winfrey herself confessed to drug use. "And I've often said over the years…in my attempts to come out and say it, I've said many times I did things in my 20s that I was ashamed of, I did things I felt guilty about, but that is my life's great big secret that's always been held over my head," she explained on her show. "I always felt that the drug itself is not the problem, but that I was addicted to the man." She added, "I can't think of anything I wouldn't have done for that man."

Winfrey's early love life was not always so tumultuous. Her high school sweetheart Anthony Otey recalled an innocent courtship that began in Winfrey's senior year of high school, from which he saved hundreds of love notes; Winfrey conducted herself with dignity and as a model student. The two spoke of getting married, but Otey claimed to have always secretly known that Winfrey was destined for a far greater life than he could ever provide. On Valentine's Day of her senior year, Otey's fears came true when Winfrey took Otey aside and told him they needed to talk. "I knew right then that I was going to lose the girl I loved," Otey recalled. "She told me she was breaking up with me because she didn't have time for a relationship. We both sat there and cried. It broke my heart." Years later, Otey was stunned to discover details from Winfrey's promiscuous and rebellious past at the end of the 1960s, and the fact that she had given birth to a baby several years before they met.

In 1971, several months after breaking up with Otey, Winfrey met William "Bubba" Taylor at Tennessee State University. According to CBS journalist George Mair, Taylor was Winfrey's "first intense, to die for love affair". Winfrey helped get Taylor a job at WVOL, and according to Mair, "did everything to keep him, including literally begging him on her knees to stay with her." Taylor however was unwilling to leave Nashville with Winfrey when she moved to Baltimore to work at WJZ-TV in June 1976. "We really did care for each other," Winfrey would later recall. "We shared a deep love. A love I will never forget."

When WJZ-TV management criticized Winfrey for crying on the air while reporting tragedies and were unhappy with her physical appearance (especially when her hair fell out as the result of a bad perm), Winfrey turned to reporter Lloyd Kramer for comfort. "Lloyd was just the best," Winfrey would later recall. "That man loved me even when I was bald! He was wonderful. He stuck with me through the whole demoralizing experience. That man was the most fun romance I ever had."

According to Mair, when Kramer moved to NBC in New York Winfrey became involved with a man whom friends had warned her to avoid. Winfrey would later recall: "I'd had a relationship with a man for four years. I wasn't living with him. I'd never lived with anyone—and I thought I was worthless without him. The more he rejected me, the more I wanted him. I felt depleted, powerless. At the end I was down on the floor on my knees groveling and pleading with him"

According to Mair's reporting "the major problem with this intense love affair arose from her lover's being married, with no plans to leave his wife." Winfrey became so depressed that on September 8, 1981, she wrote a suicide note to best friend Gayle King instructing King to water her plants. "That suicide note had been much overplayed" Winfrey told Ms. magazine's Joan Barthel. "I couldn't kill myself. I would be afraid the minute I did it; something really good would happen and I'd miss it."

According to Winfrey, such emotional ups and downs gradually led to a weight problem: "The reason I gained so much weight in the first place and the reason I had such a sorry history of abusive relationships with men was I just needed approval so much. I needed everyone to like me, because I didn't like myself much. So I'd end up with these cruel self-absorbed guys who'd tell me how selfish I was, and I'd say "Oh thank you, you're so right"and be grateful to them. Because I had no sense that I deserved anything else. Which is also why I gained so much weight later on? It was the perfect way of cushioning myself against the world's disapproval."

Nevertheless, Winfrey has remained humble and dedicated to making an impact on the world. She uses her prominent stance in society to benefit those around her.

Please have a look at my novels Wests Time Machine, and Georges Pond.

West's Time Machine

George's Pond