Here are a few of the stranger moments from those talks, the recordings of which were anonymously given to the website Factbase:

— In a 1997 appearance, Stern and Trump talked about the possibility of requiring women to get HIV tests before Trump would have sex with them. “I wouldn’t say I do this, but you could send lots of people you really like to the doctor before you ever get to know them,” Trump suggests.

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Stern then followed up on a line of questioning he had started in an earlier interview (which has been available previously, and widely discussed) in which Trump agreed with Stern’s suggestion that Trump “could have nailed” the recently deceased Princess Diana. Stern again posits that Trump “could have nailed her.”

Referring back to their discussion of HIV testing, the radio host then acted out a scene where Trump tells her to get tested first. “Hey Lady Di, would you go to the doctor?” Stern mockingly asks. Trump then gets in on the joke, imagining the conversation with the British royal. “Go back over to my Lexus, because I have a new doctor,” he says, as if addressing her. “We wanna give you a little checkup.”

As he did with many famous women, Trump proceeded to evaluate Diana’s appearance in oddly specific ways. Although he allowed that “she had times when she didn’t look great” he deemed her “supermodel beautiful.”

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“She had the height … she had magnificent skin,” he said.

— In a 2007 interview, Trump relayed a strange story about watching a Britney Spears concert a few years earlier. Back then, Trump approved of the pop star’s looks (“that was when she was saying she was a virgin … and she was so cute”), so much so that he put aside his much-discussed germaphobia. Trump recalled watching her show from the fourth row at his Taj Mahal casino. “She was sweating and looked beautiful and she threw her hat, right? Now normally if a performer throws a hat and it’s sweaty and wet and everything, I’d have no interest in it. But I grabbed that sucker,” he says. “She was so cute and wholesome and nice, I wasn’t even afraid of those germs. Today, if she threw it, I’d say ‘get that sucker out of here.’”

— In that same interview, Stern asked a caller what size her breasts were. Informed that she wore a 34C bra size, Trump said: “Not bad.” When Stern agreed, Trump waffled: “You know, could be better.”

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— In 1999, Trump boasted to Stern about his girlfriend of eight months, a model named Melania Knauss from Austria. (The now-first lady is actually from Slovenia.) Among her attributes? She doesn’t have cellulite. In fact, Trump says, she doesn’t even know what the word means. “Isn’t it nice when somebody doesn’t know what the word means?” he asked.