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Is Oprah Winfrey engaged? TV star drops telling clue

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Oprah Winfrey has sparked speculation she might be open to getting engaged again, after she was spotted wearing a huge diamond ring.

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The talk show host, 71, has been in a long-term relationship with Stedman Graham since 1986, and despite a brief engagement, they never married.

However, she sparked theories that another engagement might be on the cards while attending the 2025 American Ballet Theatre Fall Gala on October 22.

Stepping out at the event, in honour of Misty Copeland, Oprah was photographed wearing a huge diamond sparkler on her left ring finger.

Oprah Winfrey
Oprah Winfrey has sparked speculation that she is engaged after she was spotted wearing a diamond ring. (Credit: Shutterstock)
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The gorgeous piece of jewellery featured a huge diamond in the centre, and she proudly showed it off at the New York event.

Oprah loves extravagant jewellery and often wears bold jewels on her left hand, but the ring’s glitzy design and placement might lead to assumptions that she is engaged again.

Oprah and Stedman briefly got engaged in 1992, but they ultimately called it off and never married, though they remained in a committed relationship.

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The TV presenter has previously admitted she had “doubts” as soon as she said “yes” to his proposal because she didn’t want the “sacrifices” and “compromises” that come with marriage.

“I realised I didn’t actually want a marriage. I wanted to be asked,” she previously wrote in Oprah Daily.

“My life with the show was my priority, and we both knew it.”

Oprah Winfrey
Oprah showed off her gorgeous ring at the 2025 American Ballet Theatre Fall Gala. (Credit: Shutterstock)
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She calls their relationship a “spiritual partnership”, adding, “He and I agree that had we tied the marital knot, we would not still be together.”

Oprah said their relationship works because Stedman has his own identity past being her partner, and because they share “all the values that matter”, including integrity.

Oprah and Stedman have been each other’s biggest supporters over the years, and generally keep their relationship away from the spotlight.

They first met back in 1986 at a charity event and became friends, though Oprah initially brushed him off because he was often spending time with the same woman.

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Oprah Winfrey Stedman Graham
Oprah and Stedman briefly got engaged in 1992, but she called it off, realising she didn’t want to be married. (Credit: Getty)

“I thought he was nice enough, but I wasn’t that impressed. He was polite, yes, and kind,” she previously wrote in an essay.

“The sort of guy who sits with an ailing friend. Tall and handsome, for sure. But actually too handsome, I thought, to be interested in me.”

Oprah admitted she only gave him a “serious thought” months later when he had broken up with his girlfriend, and their relationship has only gone from strength-to-strength since then.

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