The talk-show host appeared on Howard Stern's SiriusXM radio show Wednesday where the veteran journalist got candid as she dished on her past dating life and her early suitors, including Bob Saget, Jeff Probst and even the King of Pop.
Recalling her date with the former Full House star, Couric said Saget "was fun, he was really fun," but admitted the comedian never called, "I had fun, I don't think I did it for him."
"I went out with Jeff Probst once too," the 56-year-old star told Stern. "I think he had puka shells on—that was kind of a weird thing."
Despite the Survivor host's interesting jewelry choice, he, too, never called Couric, although she certainly wasn't crying over either man.
"I can't say that I was devastated that neither called me back," she said. "I thought they were both nice guys... I don't think there was real magic there with either [of them], but I enjoyed spending time with them."
Katie, who is currently dating NYC banker John Molner, also shared how Michael Jackson's friend and spiritual advisor Rabbi Shmuley Boteach tried to fix the two up over a dozen years ago.
Boteach "called me in my office at the Today show," Couric recalled. "[He said] 'Katie, I have a question for you, are you seeing anyone?' And I thought, this is so beyond creepy that Rabbi Shmuley is hitting on me. I'm like 'Rabbi Shmuley, you have like nine kids, what's going on here?' I said 'Actually, I am [seeing someone].' Because I had a boyfriend at the time."
She continued, dishing additional deets on the Michael matchmaking tale: "He said, 'Oh, that's a shame...Michael [Jackson] said to me 'That's the kind of girl I would like to go out with...' and I said, 'Rabbi Shmuley, that's very flattering but I am seeing someone...will you tell him how flattered I am and what a nice compliment that is?'"
But she now wishes she accepted the offer:
"I do regret not having dinner with him. That would have been insane—breaking bread with Michael Jackson!"