
On paper, life is good for Ivanka Trump: she’s rich, she’s famous, and her father is the most powerful person in the entire world. She can do what she wants whenever she wants, and she can buy just about anything her heart desires. However, what she has in common with Donald Trump is that there’s one thing she can’t buy, no matter how much she wants it: respect from the masses!
You see, Ivanka’s relationship with her father is something of a double-edged sword. It helped make her into a celebrity and landed her a cushy government job, but this relationship ensured that she would always have the eyes of the world on her. And while the cameras were rolling, she ended up having some seriously awkward moments that would make the rest of us just want to disappear forever.
How awkward are we talking, and where can you see the cringe happening in real time? Keep reading to find out!
Attempting to crash a photo with the South Korean President

As President of the United States, Donald Trump attends plenty of major events all around the world. In 2019, he attended the G20 summit, and he brought Ivanka along for the ride. This got a bit awkward at times because even though she was a government official, Ivanka didn’t have the standing of the various national leaders in attendance. And at one point, she even got in trouble for standing too close to one of them!
Donald Trump, then-Secretary of State Mike Pompeo, and South Korean President Moon Jae-in all decided to pose for a picture. Others were in attendance, including Jae-in’s wife, and Ivanka tried to stand next to her. The only problem is that this is where Melania Trump would have stood if she had attended, making this a breach of protocol. It also annoyed Pompeo because Ivanka was blocking him, so he had to nudge her so that she would move, something she did very reluctantly.
Many criticized Ivanka for this silly photo op mistake, and some felt that this incident symbolized Ivanka’s entire time at G20. That is, she didn’t know her place and just wandered around, trying to look important!
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Getting iced out at the G20 summit

Believe it or not, that botched photo opportunity wasn’t even Ivanka Trump’s most awkward moment at the 2019 G20 summit. No, the most awkward moment occurred when several national leaders were talking among themselves about various matters of state. This included the president of France and the prime ministers of both Canada and the UK. Other big names were there, including the director of the International Monetary Fund. Oh…and Ivanka Trump.
Now, Ivanka was officially serving as a presidential aide, and you could argue that this trip transformed her into something of a low-level diplomat. But “low-level” is the keyword here, and Ivanka had no right to try to butt into the conversation with some of the most powerful people around the globe. The internet’s reaction was swift and brutal: many joked that Ivanka was like a little girl playing pretend, while others Photoshopped her (in all her befuddled glory) into various historical moments. The whole incident was bizarre enough that the French presidential palace released an official video of it, as if to ask the world a simple question: “you guys seeing this craziness?”
That time she shilled beans

For better or for worse, Donald Trump has always been a businessman. He knows how important it is to scratch someone else’s back after they have scratched his. For example, the CEO of Goya Beans, Robert Unanue, got plenty of criticism in 2020 after he praised Trump. In turn, Trump encouraged his supporters to buy Goya’s products, effectively showing solidarity with both the president and the CEO, who supported the president.
That sounds simple on paper, but it led to an insanely cringeworthy moment: Ivanka Trump, holding up a can of Goya Beans as if she were a low-rent suitcase girl on Deal or No Deal (no offense intended, Meghan!). This was a former supermodel and one of the wealthiest women in the entire world, and her famous father had her shilling cheap Mexican food products. Talk about awkward!
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All those questions about dating her dad

Strictly speaking, most of Ivanka Trump’s most awkward moments aren’t her fault…or at least, she didn’t cause them. We’re talking, of course, about all the times that Donald Trump seems to be romantically interested in his daughter. In an infamous 2006 appearance on The View, Trump was asked what he would do if Ivanka wanted to pose for Playboy.
“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. Is that terrible?” The answer, of course, is YES! That might explain why Ivanka (who was there with her father!) could only nervously grin.
That bizarre interaction changed the way the public viewed this famous father/daughter duo. For example, Trump later told a crowded rally that Ivanka (who was 35 at the time) still called him “Daddy” and that he liked it. Later, at the 2016 Republican National Convention, he gave her a handsy greeting that got way too close to her rear end. These incidents would have been weird enough on their own, but after hearing Trump openly speculate about dating Ivanka, they seem downright sinister!
