During an interview on The Pivot Podcast, Gayle King opened up about her dating experiences. Gayle disclosed that her success and fame have often posed challenges in finding a suitable partner. She shared, "What’s difficult is that people say, ‘Oh, you’re so intimidating.’ Somebody said to me once, ‘Gayle, look at your shoes … look at your bag, look at your coat. You’re friends with Oprah [Winfrey].’ A guy looks at that and says, ‘I can’t compete with that.’ But my thing is, it’s not a matter of competing. I’m not looking for someone to compete." Gayle went on to recount the incident that led her to end her relationship with her previous beau. "I went on a date. I was really excited, very excited about it," she said. "We’d gone out maybe two months, and then he said he really needed to talk to me. He wanted to have a private conversation…[he said,] ‘Do you think you could lend me $4,000?’ I’m like, oh God." Upon learning of the request, Oprah had an epic response. "You know what Oprah said, ‘God, I would have felt better if he had said $40,000,’” King explained. "I was so crushed because he was somebody who was making, you know, six figures, successful. And 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. [And I said to myself] ‘Oh God, this is just getting worse.’” Despite lending the money, the relationship didn’t endure much longer.