Oprah Winfrey and her best friend, Gayle King, often get asked for advice about a number of topics, including their 50-year old friendship.
However, in a resurfaced 2019 clip for Oprah Mag titled “The OG Chronicles,” the two were asked to give relationship advice, which turned into a counseling session.
And there was one question that Winfrey and King took no time at all to answer.
Reading her fourth question from an index card, Winfrey said, “I’ve been dating a guy, and whenever he stays over he wakes up and gets ready for work, and then we leave the house together. But I just found out through some detective work that he actually —” she stopped reading before she burst into tears of laughter.
So King cut in to add the rest which said the man “doesn’t have a job.” As Winfrey continues laughing, King reacts saying, “Yikes! Run.” She continued reading the person’s question which asked, “What should I do? Confront him or wait until he confesses to his imaginary job.”
“Oh my God” Winfrey said before agreeing with King, “This is a no-brainer.” Together they both added, “Boy, bye.”
The fans fell in love with the resurfaced six-minute clip of the besties giving relationship advice. They also touched on how to keep things spicy in a relationship, intimacy on the first date, sharing phone passwords, and what to do if the partners aren’t on the same page about building their future.
Fans responded in the comments to the video.
One person said, “I loved the way Oprah almost lost her breath for the guy who doesn’t have a job and Gayle carried on: HE DOESN’T HAVE A JOB.”
Another person wrote, “We need a series of these called “Boy Bye”. I’d watch and rewatch.”
The clip resurfaces months after Gayle King got candid about a poor dating experience she had in the past. In February 2024, King was a guest on The Pivot podcast, where she shared her uncomfortable conversation with a man she was dating.
“We had gone out maybe two months, and then he said he really needed to talk to me,” King recalled last month during her “The Pivot” appearance. She told the show’s hosts, Ryan Clark, Channing Crowder, and Fred Taylor, “He wanted to have a private conversation.”
“OK, sure, what is it?” she remembers saying to the man, before he answered, “Do you think you could lend me $4,000?”
Gayle confessed that the situation left her feeling “crushed,” especially since she was under the impression he was a six-figure earner.
“When I said, you know, ‘Could I ask what it’s for?’ He said, ‘Yeah.’ It was for a child support issue and to pay a payment on some furniture.”
Gayle loaned the man $4,000, and though he paid it back within a week, they never dated romantically again.
King’s best friend, Oprah, mocked the man’s request and allegedly said, “God, I would have felt better if he had said $40,000.”
