If you’ve spent any time on the internet over the last decade, you’ve probably seen the headlines. They range from shocked to outright disgusted. People keep asking the same question: Did he actually say that? The short answer is yes, but the long answer involves a weird, decades-long trail of interviews that make for some of the most uncomfortable transcripts in American political history.
Honestly, it’s kinda wild how many times Donald Trump has circled back to the topic of his eldest daughter’s looks. We aren’t just talking about one slip of the tongue at a campaign rally. We’re talking about a consistent pattern of "jokes" and comments that have left talk show hosts and audiences basically stunned.
That Infamous 2006 Interview on The View
The moment most people point to happened in March 2006. Donald and Ivanka were sitting side-by-side on the set of The View. Joy Behar asked him how he’d feel if Ivanka ever posed for Playboy.
Most dads would probably give a flat "no" or look for the nearest exit. Trump didn't. He started by saying it would be disappointing, but then he took a sharp turn. "I don’t think Ivanka would do that inside the magazine," he said. "Although she does have a very nice figure. I’ve said that if Ivanka weren’t my daughter, perhaps I’d be dating her."
The reaction was immediate. The other hosts groaned. Star Jones looked like she wanted to melt into her chair. Trump laughed it off, asking, "Isn't that terrible? How terrible? Is that terrible?"
The Howard Stern Files
If you want to find the really raw stuff, you have to go to the Howard Stern archives. Back when Trump was just a New York real estate mogul and reality star, he was a regular on Stern’s show. They talked about women like they were judging a dog show.
In 2003, Trump was bragging to Stern about Ivanka’s height and physique. "You know who’s one of the great beauties of the world, according to everybody? And I helped create her. Ivanka. My daughter, Ivanka. She’s 6 feet tall, she’s got the best body."
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A year later, in 2004, Stern asked Trump point-blank if he could refer to Ivanka as a "piece of ass."
Trump’s response? "Yeah."
It wasn't a "get out of my office" moment. It was a "yeah." He did add that Stern would be the last person he'd introduce her to, but he didn't blink at the terminology used for his own kid. Later, in 2006, they had a whole conversation about whether or not Ivanka had gotten breast implants. Trump assured Stern she hadn't, saying, "I would know if she did."
The Wendy Williams "Common Interests" Jolt
Fast forward to 2013. The duo appeared on The Wendy Williams Show. Wendy asked a pretty standard "get to know you" question: "What is the favorite thing you have in common with your father?"
Ivanka gave a safe, corporate answer: "Either real estate or golf."
Then it was Donald’s turn. "I was going to say sex," he quipped, "but I can't relate that to her."
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The audience gave that half-laugh, half-gasp sound. You know the one. It’s the sound people make when they aren’t sure if they just heard a joke or a confession. It was awkward. It was classic Trump.
Why Does This Keep Coming Up?
It's easy to dismiss these as "Howard Stern-era" relics, but the comments didn't stop once he hit the campaign trail. In 2015, he told a Rolling Stone reporter, "Yeah, she’s really something, and what a beauty, that one. If I weren’t happily married and, ya know, her father..."
Then there’s the more recent stuff. In Miles Taylor’s book Blowback, the former DHS official claimed that Trump’s comments behind closed doors were even worse. According to Taylor, Trump would talk about Ivanka’s "breasts" and "backside" to the point where former Chief of Staff John Kelly had to remind him that he was talking about his daughter.
Is it just a "New York" way of talking? Some supporters say he’s just a proud dad who expresses things in a blunt, hyperbolic way. They argue he’s just acknowledging she’s a beautiful woman.
Others say it’s a peek into a much darker psychological profile. Most people don't use the words "sexually attracted" and "daughter" in the same thought process, even as a joke. It breaks a social taboo that is pretty much universal.
What Ivanka Says About It
Ivanka has mostly played the role of the loyal, polished daughter. When asked about her father’s "Access Hollywood" tape or his general comments about women, she’s called them "offensive" and "inappropriate," but she usually pivots quickly to his record as an employer or his role as a father.
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She’s never publicly addressed the "I'd be dating her" comments in a way that suggests she’s bothered by them. In fact, she’s often stood right next to him while he’s made them. Whether that’s out of genuine comfort or years of practice in the Trump family business of image management is anyone’s guess.
The Bottom Line
When people talk about how Trump said he was more sexually attracted to his daughter than his wife (a quote attributed to an early draft of a Richard Cohen column), they are looking at a mountain of evidence that he views her through a lens of physical beauty first.
It’s not a conspiracy theory. It’s on tape. It’s in transcripts. It’s in books written by people who were in the room.
If you’re trying to make sense of this, here is the reality:
- The Quote exists: He did say he'd date her if they weren't related.
- The Frequency is high: This wasn't a one-time thing; it spanned over a decade of public appearances.
- The Context is usually "Shock Jock": Much of the worst stuff happened in the context of "guy talk" with people like Howard Stern, where the goal was to be as provocative as possible.
The next time this pops up in your feed, you don't have to wonder if it's "fake news." It's just part of the very public, very strange record of the 45th President.
If you want to dig deeper into the actual transcripts, your best bet is to look up the 2006 episode of The View or the 2004 CNN report on the Howard Stern tapes. Seeing the video of his body language often tells a much bigger story than the text alone. Keep an eye on the reactions of the people around him—that's usually where the real truth of the moment lies.
Next Steps for Research:
- Look for the archived video of the 2006 The View interview to see the interaction firsthand.
- Search for the 2016 CNN investigative report that compiled the Howard Stern audio clips.
- Check out the full context of the Wendy Williams interview from 2013 to see how Ivanka reacted in the moment.