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President Trump’s Awkward Moments With Ivanka

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Nicki Swift dug through two decades of footage to catalog Donald Trump’s most cringe-inducing public comments about his own daughter.

The video “President Trump’s Awkward Moments With Ivanka” pulls together clips spanning from 2004 to 2016, tracking a pattern of physical affection and public remarks that read very differently once Ivanka Trump and her husband, Jared Kushner, took official advisory roles in the West Wing. What might have passed as tabloid fodder during Trump’s reality-TV years became a genuine flashpoint once the two were working inside the White House together.

• Trump told ABC’s “The View” in March 2006, “I’ve said that if Ivanka weren’t my daughter, perhaps I’d be dating her.”
• In a 2004 Howard Stern interview, Stern called a 22-year-old Ivanka “a piece of a**” and Trump agreed; in a 2006 follow-up, Trump openly speculated about whether she’d had breast enhancement surgery, asking Stern, “Why, did she look a little more stacked?”
• On “The Wendy Williams Show” in 2013, when asked what father and daughter had in common, Ivanka said “real estate or golf” while Donald answered “sex,” prompting visibly uncomfortable laughter from the room.

The Physical Rapport That Kept Drawing Attention

The segment Nicki Swift labels “Hands-on dad” walks through years of photo shoots and public appearances where Trump’s physical contact with Ivanka went beyond the standard father-daughter hug. The clip that gets replayed most is from the 2016 Republican National Convention, where cameras caught Trump placing his hands on Ivanka’s hips as she introduced him onstage — a moment that circulated widely precisely because of how it looked next to everything he’d already said about her over the years.

The Comments That Aged Worst

Trump’s remark on “The View” wasn’t a one-off slip. It fit a pattern that stretched back to his Howard Stern appearances, where he entertained Stern’s crude commentary about his daughter’s body rather than shutting it down. The 2006 exchange in particular — Trump asking “Why, did she look a little more stacked?” in response to a breast-augmentation rumor about his own child — is the kind of exchange that, once it circulated in the context of a sitting president, drew renewed scrutiny that hadn’t attached to it during the original radio broadcast. Late-night hosts and political commentators referenced Trump’s earlier media appearances so often that they became a recurring feature of coverage on shows like The View, where his 2006 comment originated.

“I’ve said that if Ivanka weren’t my daughter, perhaps I’d be dating her.”

The Wendy Williams Moment

The 2013 joint appearance on “The Wendy Williams Show” gets singled out because it played out live, in real time, in front of an audience. Williams asked the pair a simple ice-breaker question about shared interests. Ivanka’s answer was mundane — real estate, golf. Trump’s one-word reply, “sex,” landed in the room the way it landed on video: as a joke that nobody quite knew how to laugh at.

Increased Regulatory Scrutiny Since 2016

None of this footage was new by the time it started recirculating during Trump’s presidency — the Stern interviews dated back to 2004 and 2006, “The View” comment to 2006, the Wendy Williams appearance to 2013. What changed was the context. Once Ivanka and Kushner held formal advisory positions in the West Wing, critics folded these old clips into a broader argument about nepotism inside the administration, and the RNC hip-hands photo became shorthand for a dynamic people had been uneasy about for years. Commentary comparing Trump’s remarks to other politicians’ on-air missteps became common across outlets tracking inappropriate things politicians said on live TV.

None of the clips in Nicki Swift’s rundown are new discoveries — every one of them, from the 2004 Stern interview to the 2016 convention stage, had already aired publicly years before the video stitched them together. What the compilation does is put them back to back, so a viewer who only half-remembered the “dating her” line from “The View” ends up seeing it sit right next to the RNC hip-hands photo and the Wendy Williams exchange, which is really the whole point of the exercise.