Awkward Ivanka Trump Moments That Were Captured By Millions

Sometimes, when you're the daughter of the president and an unofficial foreign advisor, it's hard to know exactly where you fall in the photo-op pecking order. This was especially apparent at the 2019 G20 summit in Japan, when Ivanka Trump, Donald Trump, and Secretary of State Mike Pompeo lined up for a photo with South Korean president Moon Jae-in. As seen in a video from CNN, Ivanka opted to stand right next to Moon's wife, Kim Jung-sook, which would presumably have been the place of the American first lady.

Since Melania Trump wasn't there, Ivanka appeared to assume she should be standing in the first lady's spot. Meanwhile Secretary of State Pompeo was left awkwardly shuffling behind the lineup, relegated to the second row while Ivanka took the limelight (via CNN). Eventually feeling Pompeo's nudge at her back, Ivanka realized she was in the wrong spot, and she somewhat reluctantly moved aside so the secretary of state could take his rightful spot. The rest of the photo-op went off smoothly, but it certainly served as a reminder that Ivanka doesn't always remember where she falls in line, sometimes literally.

It didn't take long for Ivanka Trump to realize interview questions in the political world hit a little harder than they do when you're simply the daughter of a reality TV star. We can only speculate that when Ivanka agreed to an interview with Cosmopolitan magazine, she wasn't exactly expecting Diane Sawyer. But Cosmo's Prachi Gupta brought the heat, grilling the then-34-year-old on why Donald Trump's paid maternity leave plan did not include help for male same-sex couples.

"I think that you have a lot of negativity in these questions ... so I don't know how useful it is to spend too much time with you on this if you're going to make a comment like that," Ivanka responded. Gupta pressed on, asking about Donald's 2004 assertion that "pregnancy is an inconvenient thing for a business," and continuing to question how he planned to pay for all his planned programs if there were tax cuts. Ivanka then cut the interview short after a series of flustered answers, saying, "I'm going to jump off, I have to run. I apologize." A couple days later, she tweeted, "@Cosmopolitan, your readers do & should care about issues impacting women & children. Keep the focus where it belongs — advocating change."

The tense relationship between First Lady Melania Trump and her step-daughter Ivanka Trump is no secret, but it came to a head just days before the 2020 Republican National Convention when Stephanie Winston Wolkoff's Melania and Me: The Rise and Fall of My Friendship with the First Lady hit the shelves. Wolkoff, who claims to have been close to the first lady in her book description, alleged that Melania had actively tried to prevent Ivanka from appearing in pictures at the 2017 inauguration (via The Independent). "Yes, Operation Block Ivanka was petty," Wolkoff said in a New York Magazine excerpt, adding, "But in our minds, Ivanka shouldn't have made herself the center of attention in her father's inauguration." 

In case there was any doubt, her disdain appeared readily apparent soon after at the RNC, when the first lady appeared to roll her eyes after the president invited Ivanka up onstage. Again, Twitter had a lot to say. One tweet read, "Melania Trump gives Ivanka Trump that look that 'I like you only because I have to.'"

Have you ever gone out to meet someone who was "just a friend," and instead of the usual friendly half-hug hello, they put their hands somewhere a little south of your waistline? Well, at least that person wasn't your dad. On national TV. While he was running for president. The hip-touch seen round the world still stands as one of the oddest greetings ever seen at a political convention, when Donald Trump greeted his daughter Ivanka Trump after she introduced him at the 2016 Republican National Convention by putting his hands just outside her buttocks. Yeah, this marked just one of the times Trump acted totally inappropriate toward Ivanka.

Twitter reacted as you might expect. One tweet read, "What is wrong with this man." Another asked, "Ok, so did anyone see Trump checking out Ivanka? Like, kind of patting her a**? Just asking for a friend." 

Body language expert Patti Wood told Us Weekly, "He patted her in a sexually dismissive way. That repetitive pat with open hands on that location is usually a set of body language cues to say, 'The sex with you, it was good,' or, 'That was fun sexual play.'" She added, "I want to be clear that is not even a pat you would give to a child under the age of 5. You would pat them higher up on the back."

The heiress to the Trump empire, Ivanka Trump was interviewed by Fox News in February 2019, on her thoughts regarding the Democrats' Green New Deal and what it means for Americans. "I don't think most Americans, in their heart, want to be given something," said the woman who was anointed a presidential advisor by her father. "I think that this idea of a guaranteed minimum is not something most people want. They want the ability to be able to secure a job. They want the ability to live in a country where there's the potential for upward mobility."

Never one to let stunning irony go unnoticed, Green New Deal co-author Rep. Alexandria Ocasio-Cortez tweeted, "As a person who actually worked for tips & hourly wages in my life, instead of having to learn about it 2nd-hand, I can tell you that most people want to be paid enough to live." Ouch. 

Always one to have his daughter's back, Donald Trump told a gathering of American governors a few days later that his daughter was responsible to the creation of "millions of jobs," as reported by CBS News. He did not elaborate on what, exactly, those jobs were.

Though Ivanka Trump has proven herself to be an adept public speaker, she didn't exactly leave 'em in stitches at the 2019 Gridiron Dinner. For the unfamiliar, the dinner is basically a big bi-partisan banquet where Washington's cadre of political reporters is joined by the president and several prominent members of congress. Presidents have attended all the way back to William McKinley, according to The Washington Post, but in 2019, Donald Trump asked daughter Ivanka to fill in for him.

Ivanka opened her remarks by saying she'd just been asked to speak that afternoon, possibly prefacing the fact her material would not be honed. "So I figured the funniest thing I could do was read excerpts from the Green New Deal," she said, as reported by NPR, in a possible allusion to AOC's previous Twitter comments slamming her. She continued (via The Houston Chronicle), "The press seems to think it's ironic that I, born of great privilege, think people want to work for what they are given," adding, "As if being Donald Trump's daughter isn't the hardest job in the world." Though we were not in attendance, we can imagine just a single laugh, a cough, and clinking water glasses could be heard in the background.

Donald Trump's frequent comments about daughter Ivanka Trump's appearance and relative sex appeal have been fodder for media commentary since long before he entered the political sphere. Way back in 2006, Donald was on a different kind of campaign trail, hitting the talk show circuit to promote the first season of The Apprentice. He and Ivanka appeared on The View and host Star Jones cut right into the awkwardness by asking what Donald would do if Ivanka were asked to pose for Playboy.

"I don't think Ivanka would do that inside the magazine," Donald responded. "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?" Ivanka kept a nervous smile while the hosts and audience laughed. Host Joy Behar compared him to Woody Allen. Ivanka just kept on nervous smiling.

Trump's PR team later issued a statement, as shared by USA Today, saying he was joking and making a self-deprecating comment about his tendency to date younger women — who, to be clear, were most certainly not his daughter.