According to Donald Trump, his daughter Ivanka — when she was just 17 — made him promise never to date anyone younger than her. That wasn’t a private family conversation. Trump said it aloud, into a microphone, on The Howard Stern Show in 1999, because nothing about this man’s appetite for the grotesque is ever private for long.
“I have a deal with her. She’s 17 and doing great — Ivanka. She made me promise, swear to her that I would never date a girl younger than her.”
That should have been the end of the thought. But in Trump’s mouth, the perverse always metastasizes.
“So as she grows older, the field is getting very limited.”
A father, discussing his daughter’s teenage years, not as a sacred, paternal threshold, but as the declining ceiling of his personal dating inventory. A field, he called it — as if teenage girls are livestock and his daughter just roped off the youngest of the herd. Howard Stern, equally rotten, cracked back: “The nerve of her. Now you can’t go out with 16-year-olds.” Laughter followed.
There is no transcript of the actual conversation Trump claims he had with Ivanka. But we can imagine it:
IVANKA (age 17):
“Dad, I need to ask you for something serious.”
TRUMP:
“Oh boy. I can already tell this is going to be one of those sentimental things. You want me to cry? I don’t cry. Never have. Not even when they tried to take Tiffany from me.”
IVANKA:
“I want you to promise me you won’t date anyone younger than me.”
TRUMP (laughs):
“That’s what this is about? Come on, sweetheart. I’m a very young 53. Most guys my age? Washed up. Not me. I’ve got stamina. More stamina than Jeffrey Epstein, Bill Clinton, and Prince Andrew combined.”
IVANKA:
“I’m serious.”
TRUMP:
“All right, all right. You want a deal? Fine. I won’t date anyone younger than 16….”
IVANKA:
“17.”
TRUMP:
“Fine. 17. But…”
IVANKA:
“But what?”
TRUMP:
“But if I give you that, I get something in return.”
IVANKA (nervous):
“Like what?”
TRUMP:
“Well, I still need to be able to say what I want about you on TV. You know, in a good way. Stern, Wendy, The View — they love when I talk about you. You’re very popular.”
IVANKA:
“Talk about me how?”
TRUMP:
“I don’t know, things like… ‘She’s stunning, she’s built like a model.’ That kind of thing.”
IVANKA:
“Please don’t.”
TRUMP:
“I have to. It sells. Look, if Wendy asks what we have in common, you’ll say golf or real estate or whatever — but I might say something a little more, you know, unexpected.”
IVANKA:
“What do you mean, ‘unexpected’?”
TRUMP (mock-innocent):
“Like, ‘Well, I was going to say sex.’ Then I walk it back. It’s a joke. Kind of. That’s what gets the laughs. The crowd loves it. Edgy, but charming.”
IVANKA:
“You think that’s funny?”
TRUMP:
“It’s branding, sweetheart. You don’t get it. You’re not just Ivanka — you’re Ivanka Trump. And if I treat you like a secret weapon in interviews, that only raises your value. It’s a compliment.”
IVANKA:
“You don’t see how disturbing that sounds?”
TRUMP:
“No, I see how marketable it sounds. Besides, Stern eats it up. If he calls you something flattering, I have to agree. Otherwise it’s rude. I was raised to be a gentleman.”
IVANKA:
“I’m asking you not to do this.”
TRUMP:
“And I’m telling you — this is the cost of doing business. You want the dating-age rule? Fine. You got it. But I keep my material. I need to be able to say you’re attractive. That if you weren’t my daughter, maybe I’d date you. That we have… chemistry. People like that stuff.”
IVANKA (quietly):
“No, they don’t. They just laugh because they’re uncomfortable.”
TRUMP:
“Doesn’t matter why they laugh. What matters is they remember. That’s how you stay on top. That’s how you build an empire.”
IVANKA:
“At what cost?”
TRUMP:
“Sweetheart, there’s no such thing as too far — only too boring.”
Even though we weren’t there for that imagined father-daughter conversation, you don’t need to imagine the rest. It’s all on video.
In his 1999 appearance on the Howard Stern Show, Donald Trump didn’t express pride in his daughter for setting a moral standard. He lamented that “the field is getting very limited.”
He said it like a man annoyed that the pasture is closing. A man who thinks of women — girls, really — as part of a dwindling inventory that expires with every passing year.
THIS IS STILL WHO HE IS
Trump was 53 when he said this. He was already dating Melania, who was 29 at the time. But the implication was clear: if Ivanka hadn’t set the line, there would have been no line.
In Trump’s world, a teenage daughter’s demand for decency is not a moment of reflection — it’s a practical constraint. An imposition.
It is obscene that Ivanka had to ask. It is more obscene that Trump recounted it proudly, like a man boasting of his patience.
And it is perhaps most obscene that America shrugged.
A DAUGHTER’S PLEA, A FATHER’S LECHERY
Imagine your daughter having to beg you not to chase 16-year-olds. Imagine laughing about it afterward on national radio. That is the conversation Donald Trump wanted us all to know about.
He told us who he was. And we elected him anyway. And then we did it again.
That’s not just a Trump problem. That’s an America problem.
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This post has been syndicated from Closer to the Edge, where it was published under this address.