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‘You Fumbled a Billionaire’: Oprah Winfrey Once Tracked Down a Cheating Boyfriend at His Other Girlfriend’s House and Admits She Almost Fell for His Response

Lately, Oprah Winfrey is peeling back the layers of her life and showing fans that she is a lot more like the average homegirl than she has ever let on.

First, she joked about drinking her gal pal Gayle King under the table, now, she is sharing stories about how she once followed her ex-boyfriend to his other lover’s house to bust him red-handed.

Despite seeing with her own eyes his infidelity, the billionaire media maven responded like many a deceived girlfriend, believing her lying beaux.

Oprah appeared on Sherri Shepherd’s self-titled talk show last year, where she spilled the beans.

The story was prompted by the comedian telling the OWN founder that when she was 23 years old, she was a studio audience guest on “The Oprah Winfrey Show.” The Harpo team located the footage and a fresh-faced Sherri says to Oprah, “I used to trust him. I used to trust him, but he did that ‘Baby, baby, I love you. I would never mess around on you.’ So, you feel you can trust him. Man, it’s due to men that we snoop.”

Oprah Winfrey recalls the time she caught her boyfriend cheating at his "other girlfriend's house."
Oprah Winfrey recalls the time she caught her boyfriend cheating at his “other girlfriend’s house.” (Photo by Raymond Hall/GC Images)

When they cut back to the modern-day show, where Oprah is on Sherri’s show, she talks about how she believes that women should not snoop, or else they will find something.

“This is the thing, I’ve never snooped,” “The Color Purple” producer said. “This is the thing, you need somebody where you don’t have to snoop, that’s #1. If you gotta snoop that’s already a problem.”

The O.G. talk show host scoffed at having to check a man’s phone or wallet to see if he’s up to no good.

“I’ve been there. I followed him all the way to his other girlfriend’s house,” Winfrey said about a boyfriend she had before Stedman Graham, her partner of almost 40 years.

She explained, “This was in my younger days. I followed him all the way to his other girlfriend’s house. I saw it with my own eyes and then when I said, ‘I saw you. I saw you.’ He said, ‘You gonna believe me or your lying eyes?’”

The story got more common as Oprah said she had to consider, “Well, maybe that wasn’t his car.”

Many commented on the clip of the interview that recently circulated on social media, noting that the “Beloved” star was just like them.

“People forget Oprah was just a totally normal a— lady before she got that money, I’ll always have nothing but complete respect for her,” one person wrote.

Another person “sister-girled” with Oprah, saying, “That’s EXACTLY how dudes be. Will try to convince you that you didn’t see what you saw.”

A few people joked about the low-down dirty dog and how he must feel now.

“Imagine hearing Oprah talk about how you fumbled a billionaire,” one wrote, as another wrote, “I bed oh dude probably broke and miserable and missed out on a billionaire.”

Now 70, Oprah is wiser than she was back in her 20s or early 30s. She has been with her man Stedman since 1986.

Many ask why after 38 years the two have not tied the knot. It is simple. Oprah doesn’t want to be wed.

She said in 2020 in the February issue of O, The Oprah Magazine, “In 1993, the moment after I said yes to his proposal, I had doubts. I realized I didn’t actually want a marriage. I wanted to be asked.”

“I wanted to know he felt I was worthy of being his missus, but I didn’t want the sacrifices, the compromises, the day-in-day-out commitment required to make a marriage work,” she continued.

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

The two both agreed to fall back from the marriage conversation and agreed to stay together. They call what they have a “spiritual partnership,’ and noted that Stedman, who has an estimated net worth of $10 million, is more than just “Oprah’s man.”

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