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, her father ascended to the American presidency, and her role in his administration thrust her into the international spotlight. Though she served as his "presidential advisor," she's done everything from traveling with her father on official visits to India to representing the country at major international summits. And because she wasn't necessarily a trained diplomat, this could sometimes lead to some seriously awkward situations.

But Ivanka's awkward moments weren'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 continue to stick around long after she left 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 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 then-Secretary of State Mike Pompeo lined up for a photo with the South Korean president at the time, 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.

Because Melania Trump wasn't there, Ivanka appeared to assume she should be standing in the first lady's spot. Meanwhile, then-Secretary of State Pompeo was left awkwardly shuffling behind the lineup, relegated to the second row while Ivanka took the limelight. 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 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 U.K. and Canada, the president of France, and the director of the International Monetary Fund, and that the 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. One tweet quipped that 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, 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 of 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 stands to reason that Ivanka Trump's next move would be into the world of processed Hispanic food products. 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. On "The Tonight Show," Jimmy Fallon said, "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. "That's the closest she's ever gotten to working," he said. "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, "Ok, so did anyone see Trump checking out Ivanka? Like, kind of patting her ass? 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." 

As Time noted, Ivanka was 35 at the 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, X 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."

In February 2019, Fox News interviewed Trump empire heiress Ivanka Trump 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 for the creation of "millions of jobs," as CBS News reported. 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 her 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 Hey Alma. 

At the time of this writing, Kloss doesn't follow Ivanka on any platforms, and she has diplomatically said in interviews that 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 proved 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 going all the way back to William McKinley have attended, according to The Washington Post, but in 2019, Donald Trump asked his daughter Ivanka Trump 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. "[S]o I figured the funniest thing I could do was read excerpts from the Green New Deal," she said, as reported by National Public Radio, in a possible allusion to AOC's previous X 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 People). Though we were not in attendance, we can imagine just a single laugh, a cough, and clinking water glasses 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 Newsweek noted, 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 Lucía Ramírez 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 X, "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 also quipped, "Ivanka Trump Snared by Venus Fly Trap in Unfortunate Botanical Incident."

Donald Trump's frequent comments about daughter Ivanka Trump's appearance and 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 had 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 her soon-to-be sister-in-law out of 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 fiancé 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 X, 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 X 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 face emojis. 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 her 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. 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 look 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 about it!

In one of the more intensely awkward moments from Ivanka Trump that was captured by millions, the former White House senior advisor 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 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, according to 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 her 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 for migrants, women's rights, and 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, attended the World Cup in Qatar. In fact, several photographs were 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 Instagram that they had visited the Egyptian pyramids, potentially to illustrate that they were in that part of the world anyway.

For President Donald Trump's second inauguration, held on January 20, 2025, in Washington, D.C., Ivanka Trump arrived in a forest green skirt and jacket by Dior with a matching hat and a black Lady Dior handbag with black gloves and a black belt. While the look was nice enough, Ivanka sparked strange comparisons to the outfits worn by the wives in "The Handmaid's Tale," a novel by Margaret Atwood, which Hulu adapted into a series of the same name. In the series, Serena Joy, wife of Commander Fred Waterford, is always depicted wearing tonal outfits in forest green. These outfits range from dresses and capes to skirt suits with matching hats that look much like the outfit Ivanka chose. 

Seriously, though. Why the forest green tone? It's not like it's a color that Ivanka gravitates toward often. Even stranger is how many women have emerged wearing red capes and white bonnets, the uniform of the handmaids themselves, to protest some of Trump's policies long before January 2025. Their costumes were meant to underscore threats to women's agency and autonomy, so "The Handmaid's Tale" has emerged as a timely counterpoint to Trump's presidency. There's no way that Ivanka missed this, so the fact that she chose to wear a close remake of the wives' outfits is an odd choice and a slightly eerie one. 

Protests broke out in Los Angeles in early June 2025 in response to President Donald Trump's policies on immigration. Tension ran high in the city after Immigration and Customs Enforcement (ICE) agents raided several spots in Los Angeles, arresting individuals whom they believed to be illegal immigrants. While the protests were overwhelmingly peaceful, a few who were opposed to ICE agents rioted, starting fires and throwing objects into the blazes. In response, Trump sent in the National Guard as well as the Marines to deal with the protests. 

Meanwhile, Ivanka Trump took to Instagram and posted a series of photos that made her appear blissfully unaware of what was going on in California. In honor of World Ocean Day, she wrote the caption: "There's no place I feel more free, more grounded, and more at peace than in the ocean." In the photos, Ivanka carries a surfboard, then rides a wave, then jumps on the beach. For one, the post reads as inauthentic, since it seems like more of an opportunity to show herself bathing suits. Secondly, it was terrible timing. "Your mother was an immigrant and so is your stepmother. None of you would be here otherwise," one person pointed out in the comments. "How 'let them eat cake' is this post?" another asked. "Your father gave you a good life, but many of the deportees are living in dire straits. What about their freedom?" a third stated. It was unfortunate timing. 

Not so pretty in pink. The Trump family gathered at Mar-a-Lago in preparation for Tiffany Trump's big day in November 2022. Everyone showed up, including Ivanka Trump in what many decided was a look that was far too risqué for the role of sister of the bride. For Tiffany's rehearsal dinner leading up to her wedding to Michael Boulos, Ivanka arrived wearing a pink two-piece skirt suit with rhinestone hems and a rhinestone collar. The crop top revealed Ivanka's abs, while the back of the top was held together by two black straps. 

While the outfit was objectively lovely and very flattering on Ivanka, people on X felt that it was grossly inappropriate for a family wedding celebration. Many hypothesized that Ivanka was trying to steal the show from Tiffany by wearing something so vivacious and revealing, while others simply found it tacky. "Why is she dressed like a belly dancer?" someone asked on X. "Is THAT what she wore to a wedding?!" another netizen mused. "You have to hate your sister to wear something like that to her wedding," a third stated. Perhaps for such a serious event, an outfit that wasn't so sensational might have been a better choice. Ivanka's pink getup — complete with lingerie-like back straps — was certainly distracting, and that's just bad wedding etiquette. Everyone knows that it's not polite to try to steal the show from the bride. 

Ivanka Trump and Jared Kushner are never far away from outrage, particularly after they served as senior advisors to the president during President Donald Trump's first term. While the couple firmly stepped away from politics during Trump's second term, that doesn't mean that they're free from sparking fury and outrage online. They were prominent guests at the wedding of Jeff Bezos and Lauren Sánchez on June 27, 2025. The wedding itself spurred all sorts of backlash, with protestors speaking out in Venice, noting that the wedding was just one more example of wealth inequality that Bezos embodies. Because there was such a heated reaction, many of the celebrity guests who attended were implicated in this backlash, including Ivanka and Jared. 

The Daily Beast calculated the net worth of those at the wedding, coming in at an eye-watering half a trillion dollars. Ivanka and Jared have long been criticized for their moneymaking schemes. Reportedly, while they were serving at the White House during Trump's first term as president, the two of them made between $172 million and $640 million. While they didn't take salaries, their exorbitant income struck many as questionable. Others wondered if they used their time in the White House to ensure their own financial security by prioritizing international relationships over the American people. So their attendance at the Bezos wedding struck many as an uncomfortable continuation of their elitist status.