Ivanka Trump's Most Cringe-Worthy Moments

There's no question that, of all the Trumps, President Donald Trump is the one who gets the most flack, but the apple sure doesn't fall far from the tree. Trump's second-oldest child, Ivanka Trump, has had her fair share of controversy over the years — much of which she appears to have brought upon herself. From the time she was introduced to the world as an up-and-coming model in her early teens, the businesswoman has encountered a significant number of critics, thanks in large part to Ivanka's numerous shady comments and actions.

Ivanka has always been close to her father (from appearing beside him on The Apprentice to working for the Trump Organization from 2005 to 2017 and eventually joining him in the White House), which, unfortunately, hasn't done much for her reputation. Rather than keeping her head low and working hard, she's repeatedly tried to insert herself into the limelight, and it's backfired — big time. Here are Ivanka Trump's most cringe-worthy moments.

In 2009, Ivanka Trump published her first book, The Trump Card: Playing to Win in Work and Life, a 260-page "business book for young women on how to achieve success in any field, based upon what Ivanka Trump has learned from her father and from her own experiences." Unfortunately, it seems those young women weren't quite looking for her advice.

The tome received lukewarm reviews on sites like goodreads, which likely had something to do with the fact that it was full of cringe-worthy quotes. While some statements were simply confusing — "Success isn't something that happens to you; you happen to it" — others were completely tone-deaf. For example, writing about sexual harassment, Trump noted that it is "never acceptable," but added, "At the same time ... learn to figure out when a hoot or holler is indeed a form of harassment and when it's merely a good-natured tease that you can give back in kind."

She even appeared to allude to the idea of #fakenews long before her father ever did, writing, "Perception is more important than reality. If someone perceives something to be true, it is more important than if it is in fact true," she continued. "This doesn't mean you should be duplicitous or deceitful, but don't go out of your way to correct a false assumption if it plays to your advantage." Ivanka, just stop. 

When Redbook published Ivanka Trump's Guide to Looking Like a Boss in 2012, it included a number of pretty standard sartorial tips and trips, but one did stand out. "A timeless piece of jewelry, like pearls or stud earrings, has lasting value," Trump told the outlet. "I bought a vintage ring for $600 with my first paycheck; I plan to pass it down to my daughter."

The problem is that Ivanka's first paycheck (and most of the ones that followed) was largely made possible thanks to her family connections. Connections that also allotted her the privilege to blow an entire paycheck on a piece of jewelry because other mundane bills, like rent, were being taken care of. As The New York Times asked back in 1997 when a 15-year-old Ivanka Trump was getting her start in modeling, was her success due to "her cheekbones (high) or her name (Trump)?" According to the article, it seemed like the latter. For one, the agency that signed her (Elite Modeling) had "a longstanding, informal relationship" with Donald Trump. What's more, Michael Flutie, owner of a competing agency called Company Management, told the paper that if Ivanka had "walked into my agency, I would not sign her as a model [...] I don't think she has that edge." Ouch.

Donald Trump has long been involved in beauty pageants and reality TV and, as Jezebel uncovered, in 2013, he tried to merge the two in an effort to launch his daughter's own television career. According to sources who spoke with the outlet, Ivanka Trump was gearing up to host Trump Town Girls, a reality competition whose premise sounds incredibly sexist.

Although the show never made it to air, Jezebel gained access to press materials and clips from the pilot episode, which was being produced for E!, and deduced that its main premise was "pitting beautiful, leggy contestants in Trump's beauty pageants against the hardened real estate brokers of Trump International Realty." Apparently, teams of two women were tasked with competing to see who could earn the most commissions in any way possible. As the outlet noted, the clips portrayed the women as being "intensely competitive and catty with one another, aware that working for Trump International means being replaced at any time with someone hotter." Yikes.

Luckily for Ivanka, the show lacked the necessary star power to move forward, and, soon enough, all mention of its existence was wiped from the Internet before it ever saw the light of day.

President Trump's relationship with his daughter has been heavily scrutinized over the years as he has amassed, what The Independent calls, an "unsettling record of comments," like the time he casually told The View in 2006, "I've said if Ivanka weren't my daughter, perhaps I'd be dating her." Needless to say, there have been countless times where Trump has acted totally inappropriate towards his daughter.

While it's not often that Ivanka Trump's part in the relationship is explored, in September 2017, she became the subject of great Twitter ridicule when it was revealed that she still refers to the POTUS as 'daddy.' It was the President himself who, while inviting Ivanka to join him up on stage during a speech in North Dakota, told the crowd, "She's so good, she wanted to make the trip. She said, 'Dad, can I go with you?' She said actually, 'Daddy, can I go with you?' I like that, right?"

Although Ivanka brushed off the comment, video of the proclamation soon began making the rounds on Twitter as it was shared by reporter David Mack who quipped, "The replies to this tweet are why I re-downloaded Twitter." In addition to countless gif replies showing people either shocked or throwing up, one user slammed, "So the moral of this story is that @Ivanka doesn't have anything to do so she wants to take a ride on the big airplane with her daddy."

When Fox News asked Ivanka Trump in February 2019 to comment on Rep. Alexandria Ocasio-Cortez's Green New Deal, "guaranteeing a job with a family-sustaining wage, adequate family and medical leave, paid vacations, and retirement security to all people of the United States," the POTUS' daughter had quite the reaction.

"I don't think most Americans, in their heart, want to be given something," she began, justifying, "I've spent a lot of time traveling around this country over the last four years. People want to work for what they get." She went on, "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." Trump went on to point out that she believes the U.S. is doing better than it has in recent years and that "it stands in quite sharp contrast to the rest of the world," which she claimed "has slowed down." 

Alexandria Ocasio-Cortez quickly took to Twitter to clap back, pointing out Trump's inadequacy to speak on behalf of the average American worker. She wrote, "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. A living wage isn't a gift, it's a right," she proclaimed. "Workers are often paid far less than the value they create."

Here's something you might not know about Ivanka Trump: Her sister-in-law is none other than Karlie Kloss. Lost? We got you. It's because the supermodel is married to Joshua Kushner a.k.a. the brother of Jared Kushner a.k.a. Ivanka Trump's hubby.

If you're a fan of Kloss, this news will likely come as a surprise, as she has rarely spoken publicly about their family connection. However, if you follow the POTUS' daughter on social media, you'll know she's repeatedly gushed about being related to Kloss. Yup, their relationship appears to be painfully one-sided.

In July 2018, for example, Trump gushed over Kloss' engagement announcement on Instagram, commenting, "I feel blessed to have you as a sister (!!!) Karlie and look forward to the decades of happy memories we will create together as a family!" In March 2019, she shared a video of herself watching Kloss hosting the Season 17 premiere of Project Runway in which she screamed with excitement, "Karlie, it's happening!"

Sadly, Kloss has never responded to any of these signs of affection, nor does she follow Trump on social media, as Express unearthed. In fact, during an interview with British Vogue, Kloss said of being related to the President's family: "It's been hard. 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," she concluded.

When President Trump decided not to attend the 2019 Gridiron Club Dinner, which got its start in 1885 and is described by the Washington Post as an "exclusive gathering of politicians and media elite," he sent his daughter on his behalf. Traditionally, the evening is kicked off by the President, who shares some "jokey remarks" before "a prominent Democrat and Republican" do the same, all leading up to a number of comedic sketches performed by top journalists.

Clearly doing her best to stick to tradition, Ivanka Trump tried to show off her sense of humor at the top of the evening, but as the Washington Post reported, she bombed in front of 700 guests. Revealing that she had been asked to attend the dinner that same afternoon, she quipped, "The press seems to think it's ironic that I, born of great privilege, think people want to work for what they are given. As if being Donald Trump's daughter isn't the hardest job in the world," she deadpanned. Cue the crickets.

In May 2018, President Trump and his administration made headlines when they introduced a new policy that called for the separation of families who crossed the US-Mexico border illegally. As Vox revealed, adults caught by Border Patrol between ports of entry were to be "transferred to criminal custody" while their children would be labeled "unaccompanied minors" and "sent into the care of a totally separate government department."

Initially, Ivanka Trump spoke out against family separation, but when Face the Nation asked her about the subject in December 2019, she tried to wash her hands of the issue. "We went and looked, and Homeland Security says there's still around 900 children who remain separated from their families," host Margaret Brennan told Trump, asking, "Is that something that you continue to remain engaged on?"

Rather than giving a definite yes or no response, Trump deflected responsibility, saying, "Well, immigration is not part of my portfolio." Yikes. She continued, "Obviously, I think everyone should be engaged and the full force of the U.S. government is committed to this effort to border security, to protecting the most vulnerable."

Still not answering the question, she then switched gears and went on a confusing tangent, talking about human trafficking and praising her father. She added, "That includes those being trafficked across our border, which this president has committed to countering and combatting human trafficking in an incredibly comprehensive and aggressive way."

The official White House website may have once had Ivanka Trump listed as 'Advisor to the President,' but her role has been the topic of many questions and great debate since Day 1. And it's not just Americans who appear to be confused by her duties. When Ivanka Trump appeared at the G-20 summit in Osaka, Japan, in July 2019, it was a whole slew of world leaders who publicly turned on her.

In a video, which was originally posted by the @elysee Twitter account (aka the French presidential palace), Trump was shown trying to awkwardly take part in a conversation with French President Emmanuel Macron, British Prime Minister Theresa May, Canadian Prime Minister Justin Trudeau, and IMF managing director Christine Lagarde, and being repeatedly snubbed. The exchange was truly cringe-worthy and inspired the #UnwantedIvanka meme, which saw folks photoshopping Trump into famous scenes, like a Mean Girls movie still with the caption "She doesn't even go here," or the iconic Beatles Abbey Road photo. Meanwhile, Rep. Alexandria Ocasio-Cortez savagely tweeted, "It may be shocking to some, but being someone's daughter actually isn't a career qualification."

While Trump didn't comment on the awkwardness, she definitely must have felt it. As body language expert Patti Wood summarized to Refinery29, "She stood slightly outside the circle, in a way that shows she felt unwelcomed. Also, the group didn't turn toward her to allow her in fully." Awkward!

Ivanka Trump's appearance at the 2019 G-20 summit was by no means the only eyebrow-raising work trip the First Daughter has taken since her father became POTUS in January 2017.

In September 2019, for example, she flew to Bogota, Colombia, where she met with the country's president and vice president, inaugurated the Academy of Women Entrepreneurs, and visited a Venezuelan migrant camp. While Colombian Vice President Marta Lucía Ramírez explained to local paper El Tiempo that the trip's mission was to "show her the different projects we have for the economic empowerment of women," things didn't quite turn out that way.

First, a slight wardrobe malfunction (in which wind wreaked havoc upon Ivanka Trump's statement sleeves) stole the show and made the rounds on Twitter, then media began to turn on her with the New Zealand Herald dubbing the trip "a mission of benign diplomacy" and GQ asking, "What about the immigrant detention camps here in the U.S.?"

Just a few months later, in February 2020, Trump's travels were criticized again when she joined the President on a state visit to India. While Vogue begged the question, "What exactly is Ivanka Trump doing in India?", The Huffington Post didn't hold back when it proclaimed, "Americans can't figure out what Ivanka Trump is doing in India. Besides tagging along with dad on the taxpayers' dime."

In October 2019, Ivanka Trump took to Twitter to praise the Justice Department's arrest of 330 individuals and rescue of 23 children in what the Department described as a "takedown of the largest darknet child pornography website." After tweeting a link to the Department's official press release, Trump shared a warning with the world, writing, "Our message for those who produce, distribute and receive child pornography is clear: You may try to hide behind technology, but we will find you and we will arrest and prosecute you."

Unfortunately, despite the news being worthy of praise, as Queerty noted, things "got really awkward really fast" as the Twitterverse turned on Trump. The response was harsh, to say the least, as users pointed out the hypocrisy of her tweet, highlighting her father's friendships with convicted sex offenders. "George Nader visited the White House 13 times," one user noted, while another pointed out, "Your dad was good friends with Jeffrey Epstein." Another critic went as far as to accuse the president of "traffick[ing] young women through his modeling agency," while some simply took offense with Ivanka Trump's choice of words. As one user clapped back, "Ivanka said 'We' did this. Ivanka did absolutely nothing." Cringe, indeed.