It Was Very Uncomfortable—Oprah Winfrey’s Ex-Boyfriend Reveals What It Was Like Dating Her

Credit: DepositPhotos
Credit: DepositPhotos

Long before Oprah Winfrey became a global media powerhouse, she had a brief romance with a young TV reporter named John Tesh—and now he’s looking back on it.

Tesh, 73, recently reflected on dating Winfrey in the 1970s when the two were rising broadcasters in Nashville, Tennessee. At the time, they worked for competing local television stations, and their relationship drew attention—especially given the social climate of the South during that era.

“It was very uncomfortable back then for an African-American woman and a very, very white guy to be dating,” Tesh said, describing the pressures they faced as an interracial couple.

Despite the outside noise, he insists they didn’t let public reaction define their time together. Because their work schedules were intense, they only managed to see each other about once a week. The scrutiny they faced eventually became something they joked about privately.

“One of us would say, ‘Which restaurant do you want to clear out tonight?’” he recalled, referring to the stares and attention they sometimes received.

Credit: DepositPhotos
Credit: DepositPhotos

Even in those early days, Tesh said it was clear Winfrey was destined for something bigger. “We all knew she was something special,” he shared, adding that he especially enjoyed when they were assigned to cover the same stories. “It made work a lot more fun.”

As their careers took off, the relationship naturally came to an end. Winfrey moved first to Baltimore and later to Chicago, where she built the empire that would make her one of the most influential women in the world. Tesh headed to New York and Los Angeles, eventually becoming a longtime co-host of Entertainment Tonight.

In 1996, he left the show to focus on music, composing the now-iconic “Roundball Rock” theme for NBA on NBC and launching a successful concert career that has supported PBS programming for years.

Both went on to find lasting love elsewhere. Tesh married actress Connie Sellecca in 1992. Winfrey has been in a committed relationship with Stedman Graham since 1986.

Looking back decades later, Tesh’s memories offer a glimpse into a lesser-known chapter of Oprah’s life—one shaped by ambition, young love, and a relationship that quietly unfolded before the spotlight became blinding.

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