‘It’s Hard Out Here for a Pimp’: Gayle King Says She Still Struggling to Find a Man After Once Helping a Man Pay His Child Support on a Date

In the words of Terrence Howard’s “Hustle & Flow” character, “It’s hard out here for a pimp,” says Gayle King.

Despite living her best life as the lead host of “CBS Mornings” and co-hosting with Charles Barkley on CNN’s at least temporarily canceled “King Charles,” the Sports Illustrated cover girl continues to lament her single status and the challenges of navigating the dating scene.

Earlier this year, the broadcast journalist opened up on the “Pivot” podcast about a bizarre dating experience where a man asked her for $4,000 for furniture and child support on their first date.

Gayle King struggling to find a date
Gayle King says she still has trouble finding a man following her Sports Illustrated cover shoot. (Photo by Arturo Holmes/WireImage)

In a recent appearance on the “Tamron Hall” show in May, she explained that finding someone to couple up with has been challenging because of a few factors, mostly her wealth, age, and celebrity.

“It’s hard out here for a pimp,” King said to Tamron Hall during her visit. “That’s what I said! Yeah, I said it. The struggle is real.”

When asked if she’s tried dating apps, the 69-year-old shared the roadblock there.

“This is the thing, if I could go on a dating app and people didn’t know it was me, yeah, I would do it. But I think it’s hard when you are a public person,” King shared before adding that she would probably date “a friend of a friend.”

But Oprah’s bestie has a hard no when it comes to dating married men and men with girlfriends. However, she is open to getting to know someone younger than she is — the only caveat there is that he can’t be too much her junior.

“I don’t want to date somebody I could have given birth,” she says, “I don’t want to be a nurse or a purse.”

While money is not a thing for King, she said it is important to be with a man that “has their own business,” and is “very confident in their own skin.”

King’s remarks about dating has sparked discussion around whether or not it is appropriate to date someone when they are broke. While discussing her one of her bad dates, where the suitor asked her for four figures, one person said, “Never ever ask a woman for money, whatever respect she had for you will be ripped for shreads.”

Another understood her dilemma and wrote, “When youre rich, limiting your dating pool to the 1% of people on your same level seems like an unnecessary shrinking of your options. I still aint paying no one else’s child support tho.”

One thing that is important to King, according to her interview with Hall, is getting with someone that celebrates her and gets excited for her when she is doing her.

As the dating conversation came to a close, the mother of two said she wanted any potential boo to know that although she is booked and busy, she is never “too busy for the right person.”

Fans in the YouTube comment section loved how open King was, applauding how easy an interview she gave and how personable she seemed. Some even gave words of encouragement regarding dating for her and other viewers.

One comment read, “Someone tell Gayle there’s a celebrity dating app out there. It’s how David Harbour from Stranger Things met singer Lily Allen.”

“So 1975 and under is a no. Go head Gayle, live your best life,” another jokingly remarked, as someone else said, “Gayle King might just need to go on the Steve Harvey show for some match making.”

A fourth person added, “I love Gayle. Your light is bright. Hard for a man to step in that world. Idk who some of Gayles matches??”

Even though King has not found that special one, she is not giving up. She told Hall that she wanted the men to know that she is “alert and available.” Just waiting for the right one to step up, no matter how hard that might be, and be her happily ever after.

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