Awkward Ivanka Trump Moments That Were Captured By Millions

Donald Trump's daughter Ivanka Trump has been no stranger to the limelight. Though she started her career as a teen model and went on to run her own clothing line, as her father ascended to the American presidency, her role in his administration thrust her into the international spotlight. Though she's currently listed as a "presidential adviser," she's done everything from traveling with her father on official visits to India to representing the country at major international summits. And as she's not necessarily a trained diplomat, sometimes it can lead to some seriously awkward situations.

But Ivanka's awkward moments aren't limited to international events. Between her father's sometimes questionable comments about her appearance (and handsy greetings) and her straddling the worlds of celebrity and politics, Ivanka has given us all some cringeworthy moments that will stick around long after she's gone from politics. From wardrobe mishaps to social media snubs, here are some of Ivanka Trump's most awkward public appearances.

Sometimes, when you're the daughter of the president and an unofficial foreign adviser, 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.

Have you ever been at a party talking with three or four of your best friends when some person nobody invited stands around you desperately trying to butt in? Yeah, now imagine your crew consists of the prime ministers of the UK and Canada, the president of France, and the director of the International Monetary Fund, and that party crasher is a fashion model-turned-unofficial diplomat. To say that collection of leaders looked massively confused as to why Ivanka Trump was there would be an understatement. It was so painful that the French presidential palace released a video of it, according to a tweet from the BBC's Parham Ghobadi.

Donald Trump's detractors didn't waste a minute pouncing on the incident either, with tweets like one quipping this was the "very reason there's a table for adults and one for children." International Monetary Fund Managing Director Christine Lagarde's side-eye got some love too. But perhaps the best viral trend to come from the incident were the photos of Ivanka spliced into major historical moments, from Martin Luther King's "I have a dream" speech to the invasion of Normandy (via The Guardian).

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."

After years as a fashion model and arbiter of style, it only reasons that Ivanka Trump's next move would be into the world of processed Hispanic food products, right? This would have seemed to be the case in July 2020, when Ivanka tweeted out a picture of herself holding up a can of Goya black beans with the caption, "If it's Goya, it has to be good. Si es Goya, tiene que ser bueno." And though she did it to support Goya in the wake of a political controversy, she looked about as natural holding the can as an elephant holding a pastry brush.

Late-night talk show hosts piled on, with Jimmy Fallon saying, "I'm not sure if Ivanka's trying to promote Goya or she's auditioning to be a model on 'The Price is Right.'" Seth Meyers was slightly less diplomatic, saying, "That's the closest she's ever gotten to working. You just know she's sore today. This looks like a confusing ad you'd see on the side of a bus" (via Chicago Tribune).

The tense relationship between first lady Melania Trump and her stepdaughter 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.'"

Who can forget the legendary "Simpsons" episode in which Homer finds he can finally bond with Lisa over gambling on football games? Well, that seems downright pastoral when juxtaposed with Donald Trump and Ivanka Trump's 2013 interview on "The Wendy Williams Show," when the host's attempt at showing the world how celebrity father-daughter teams bonded took a big turn for the weird.

During a segment called "Fave Five," host Wendy Williams asked both Trumps what they had most in common. "Either real estate or golf," Ivanka diplomatically answered. But then Donald piped in, "Well, I was going to say sex, but I can't relate that to her." 

Ivanka then gave the world the universal face for "Ew, Dad, gross!" before Williams awkwardly moved on to the next question. The interview had stayed mostly buried until 2016, when Us Weekly found a clip and ran it just before the election.

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 around 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, "Okay, 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 oddly inappropriate train just kept on chugging along with Donald Trump and Ivanka Trump, making a stop at a North Dakota rally where the president was giving a speech on tax reform. Though he didn't delve into why exactly Ivanka needed to be present, Donald did give the crowd a bit of a clue, saying, "She's so good. She wanted to make the trip. She said, 'Dad, can I go with you?' She actually said, 'Daddy, can I go with you?' I like that." 

Ivanka was 35 at the time, we might add, as noted by Time.

Ivanka mostly ignored the comment. Instead, she gave some brief comments to the energy workers assembled at the rally, saying, "We love this state, so it's always a pleasure to be back here. You treated us very very well in November and have continued to, so we like showing the love back." Predictably, Twitter had a lot to say about it, and one user probably said it best when they tweeted, "So the moral of the story is that [Ivanka] doesn't have anything to do so she wants to ride on the big airplane with her daddy."

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 adviser 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 for the creation of "millions of jobs," as reported by CBS News. He did not elaborate on what, exactly, those jobs were.

There is nothing quite like the pain of posting a big, gushing video about someone and getting ... crickets. Just ask Ivanka Trump, who seemed absurdly excited for her supermodel sister-in-law Karlie Kloss' debut as host of Season 17 of "Project Runway." The night of the premiere in 2019, Ivanka tweeted a giddy video in which she said, "Gosh, Karlie, it's happening!" Kloss left her hanging — no like, no mention.

It wasn't the first time Kloss had dissed the wife of husband Josh Kushner's brother. When Kloss announced her engagement on Instagram, Ivanka commented, saying she was looking forward to creating happy memories as a family. But Kloss didn't respond, and the comment has since been deleted, according to Alma.com. 

At the time of this writing, Kloss doesn't follow Ivanka on any platforms, and she has diplomatically said in interviews she prefers to distance herself from the first family. "It's been hard," she said in an interview with Vogue U.K. "But I choose to focus on the values that I share with my husband, and those are the same liberal values that I was raised with and that have guided me throughout my life."

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 bipartisan 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, "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" (via The Houston Chronicle). 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.

We've all had that unfortunate moment when you think you've got your look absolutely nailed, you walk outside, and a big gust of wind instantly undoes an entire morning of styling. But, hey, at least you weren't standing next to the vice president of Colombia in front of hundreds of international photographers. Such was the fate of Ivanka Trump when she set out on an official visit to Colombia to promote the Trump administration's Women's Global Development and Prosperity Initiative.

While the trip was successful and Ivanka got to meet the group's first participants, as noted by Newsweek, her work was collectively pushed to the back burner when the military-green dress she wore got caught in a blast of wind during a photo-op with Vice President Marta Lucia Ramirez and Minister of National Defense Guillermo Botero. The bell sleeves popped all the way back to her shoulders, prompting The Daily Beast's Molly Jong-Fast to dub it on Twitter, "the dress that launched a thousand gardening jokes."

That was one of the nicer ones. Jong-Fast also joked that Ivanka was "reforesting the Amazon one couture dress at a time." Writer Steve Silberman quipped, "Ivanka Trump Snared by Venus Fly Trap in Unfortunate Botanical Incident."

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 nervously 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.

Things got really awkward when Ivanka Trump cut out her soon-to-be sister-in-law from Tiffany Trump's wedding photos. In November 2022, the whole Trump crew met up at Mar-a-Lago in Palm Beach, Florida, for Tiffany and Michael Boulos' nuptials. Naturally, partners came along, and Kimberly Guilfoyle joined her fiance Donald Trump Jr. at the celebration.

However, it seems like the dress code for the event was pastels and soft hues. All of the guests, especially the Trump women, adhered to this code. All except Guilfoyle, who wore a black dress and black and silver strappy heels. And with this fashion faux-pas, it seems like Guilfoyle didn't make the cut, literally.

On social media, Ivanka posted a photo of Lara Trump, Marla Maples, Tiffany, Melania Trump, and herself standing together at the wedding. "Wishing @TiffanyATrump and Michael an abundance of happiness and joy as they begin their lives together as husband and wife! May their love be a source of light in this world!" Ivanka wrote on Twitter, along with the photo. People were quick to notice that Ivanka had cut Guilfoyle out of the photo. "Ivanka cropped out Kimberly Guilfoyle from Tiffany's wedding photos," someone noted on Twitter with a "LOL." "Why did you cut Kimberly out?" someone else asked. A few hours later, Ivanka shared a photo with Guilfoyle included on her Instagram stories, along with three happy emoji. Even if it were just an innocent mistake, the whole thing was super awkward.

Following her time in the White House, Ivanka Trump seemed to follow her bliss by spending lots of time with hubby Jared Kushner and their children, doing nonpolitical things. Her Instagram account, on the rare occasions that she updated it, was dotted with photos of herself and her family traveling, having fun, and relaxing. Oddly enough, one of these posts went viral, and not because people were so interested in her pursuit of leisure.

On September 18, 2022, Ivanka posted a video on Instagram of herself wakesurfing behind a boat in Miami, Florida. People had the strangest reaction to it, claiming that Ivanka faked the video and was wakesurfing in front of a green screen. "Fake," one person commented. "Photoshopped," someone else added. "Sorry [but] it looks green-screened," another person said.

Ivanka was nonplussed by these comments, though, because a year later, on September 5, 2023, she posted new content of herself wakesurfing again. People seemed to have the same reaction yet again. "Love her but the photo and video looks fake. Her feet did not get wet at all," one person said in the comments. Well, despite the criticism, Ivanka clearly won't stop wakesurfing, or posting content about it!

In one of the more intensely awkward moments from Ivanka Trump that was captured by millions, the former White House senior adviser spoke out against former President Donald Trump to the House Committee. Ivanka offered testimony about the events that took place on January 6, 2021, as well as her take on President Trump's claims that there was election fraud.

The Trump family has famously offered a united front, portraying themselves as the connected family standing up to a media barrage against their bombastic patriarch. However, when Ivanka testified, this facade fell apart. While speaking to the committee, Ivanka agreed with Attorney General Bill Barr that there was no evidence of election fraud. "I respect Attorney General Barr. So I accepted what he was saying," Ivanka said, per The Guardian. She also notified the committee that President Trump had indeed watched the violence that occurred on January 6 and was well aware of what was happening at the Capitol.

While this level of betrayal must have certainly been intense between the father and daughter, it's clear that Ivanka was committed to making a comeback, along with husband Jared Kushner, after their stint in the White House. And no matter how awkward the testimony was, Ivanka has been clear about separating herself from her father's future political ambitions.

The 2022 FIFA World Cup in Qatar was a very controversial event, boycotted by many celebrities and A-listers because the sovereign state has controversial policies around migrants, women's rights, and those of the LGBTQ+ community. So many in positions of influence spoke out against the country, claiming that it wasn't right to attend the event simply because of the location.

However, Ivanka Trump, Jared Kushner, and their three children, Arabella, Joseph, and Theodore, attend the World Cup in Qatar. In fact, there were several photographs taken of Ivanka and Jared talking with and watching the matches from a private box with Qatar's prime minister, Khalid bin Khalifa bin Abdulaziz Al Thani. They also spent time with Qatari billionaire Nasser Al-Khelaifi, who's also the president of French soccer club Paris Saint-Germain. Ivanka wore an all-white midi-dress to the event with long sleeves and a high neckline. Her children and husband were dressed casually.

The controversial trip to Qatar came on the heels of an extended family trip to the Middle East. Shortly before the World Cup, Ivanka posted on social media that they had visited the Egyptian pyramids, potentially to illustrate that they were in that part of the world anyway.