Back in the 1980s, Oprah Winfrey introduced the heavy topic of ‘commitment’ to Reginald Chevalier, the man she was enamored with just months after their first meeting.
From the moment she laid eyes on filmmaker Reginald Chevalier, Oprah acted swiftly and with determination, viewing him as her ideal partner. Their first encounter occurred during a look-alike segment on her show in 1985, where Reginald was said to resemble Billy Dee Williams. Once the segment concluded, Oprah issued a stern warning to her staff—if they permitted him to leave, they would face termination—and ordered them to ensure he stayed backstage.
Reflecting on their time together, Reginald reminisced about moments spent in Oprah’s water tower condo, saying, “I remember how she loved taking candle-lit baths before going to bed.” He added, “We enjoyed many of them together.”
He felt that Oprah was eager to settle down and perceived himself as the ‘chosen one’, with marriage frequently being a topic of discussion.
However, an unexpected shift occurred in April 1986 when Oprah, acting coldly, locked Reginald out of her condo, leaving his belongings at the front desk. Accompanying his possessions was an envelope stating, ‘Sorry, things aren’t working between us. Oprah Winfrey.’ The breakup was devoid of any further communication—no calls, no farewells, only the concierge noting the locks had been changed. Clearly, there was no opportunity for a final intimate encounter.
Oprah didn’t even summon one of her staff members for a final rendezvous, missing the chance for one last steamy bath together.
