When Ivanka Trump was 17 years old, she reportedly set an age limit for the women that dad Donald Trump was allowed to date. "I have a deal with her," Trump said of his daughter during a taping of The Howard Stern Show in June 1999. "She's 17 and doing great — Ivanka. She made me promise, swear to her, that I would never date a girl younger than her." The New York Daily News pointed out that 17 is the age of consent in New York, "so Trump essentially told Ivanka that he wouldn't violate statutory rape law."

Trump then proceeded to joke with Stern that his deal with Ivanka meant "as she grows older, the field is getting very limited." "The nerve of her," Stern said in response. "Now you can't go out with 16-year-olds." At the time of the interview, Trump was already dating his current wife Melania, who is 24 years younger than him — but 12 years older than Ivanka.

Of course, Trump was no stranger to Stern's show, having called in repeatedly throughout the 1990s. In another interview no less cringe-inducing, Trump in 1995 discussed with Stern how annoying women's accents could be — or, as Stern phrased it, how "one day the accent is cute and the next you're married to Dracula's sister." "You know what I like most about Marla [Maples, Trump's second wife]? And this is not lewd," Stern said. "No accent. Because that can make you bonkers after a while. Isn't that true?"

Yes, Trump agreed: "Especially when they're asking for money."