Here are Ivanka Trump's 5 Most Embarrassing Moments on National Television

Here are Ivanka Trump's 5 Most Embarrassing Moments on National Television
Cover Image Source: Getty Images | Photo by Sylvain Gaboury

Looking Back at Ivanka Trump's Top 'Cringe' Moments on TV

Image Source: Getty Images | Photo by Sean Gallup
Image Source: Getty Images | Photo by Sean Gallup

 

Ivanka Trump is a socialite and former political enthusiast who is better known as Donald Trump’s daughter. The former President’s daughter was involved in her father’s company, the Trump Organization, up until 2017, after which she quit. Ever since the twice-impeached former President announced his run for the Presidency in 2024, Ivanka strongly claimed that she “does not plan to be involved in politics” any longer in 2022. Since then, she’s been focused on taking care of her family and has been having an active social life. However, she’s back in the limelight after she was recently called to testify against her father and brothers in the ongoing Civil Fraud Case Trial. Nevertheless, the socialite is used to being in the spotlight and has been invited to many renowned shows that interview her. Although she’s generally known to have a very composed and cool demeanor, take a look at some of the times she’s cringed on TV through the years, as reported by Style Magazine.

1. Miss Teen USA Beauty Pageant

Image Source: YouTube | @21stcenturyafropolitan
Image Source: YouTube | @21stcenturyafropolitan

 

Ivanka is known for her dazzling personality and her elegant fashion choices whenever she’s out in public. The former Trump campaign adviser was always a fashion enthusiast and made her debut on television when she was just a 15-year-old teenager. Ivanka hosted her dad’s Miss Teen USA Beauty Pageantway back in 1997. As per a 2019 book, Kushner, Inc.:Greed. Ambition. Corruption. The Extraordinary Story of Jared Kushner and Ivanka Trump, authored by Vicky Ward, the teen was “horrendously nervous” throughout the pageant. This led to many errors while on air and some rather awkward and inappropriate comments. During a swimsuit round, she said to a model, “I can guarantee my brothers were loving that. Are any of you single?”

2. Donald Trump's Reaction to Her Posing for Playboy Magazine on The View

Image Source: YouTube | @FUSION
Image Source: YouTube | @FUSION

 

The View is perhaps one of the most incredible daytime talk shows that discuss current affairs with an array of guests from different backgrounds. In 2006, the show invited none other than Trump and his daughter, Ivanka, for an interview. During a series of discussions about different affairs, Ivanka’s dad was asked by former host Star Jones about his reaction if Ivanka desired to appear in the famous Playboy magazine. After a moment's thought, he said, “I don’t think Ivanka would do that inside the magazine.” Although the hosts at the time thought it was his final answer, he continued to add a rather bizarre statement: “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?” Even though this statement was brushed off as a joke and nothing serious, Ivanka had a look of utter discomfort and awkwardness registered on her face.

3. When Andy Dick 'Accidently' Groped Her on TV

Image Source: Getty Images | Photo by G. Gershoff
Image Source: Getty Images | Photo by G. Gershoff

 

As per People, comedian Andy Dick got plenty of backlash after he reportedly touched Ivanka on her thigh in a very inappropriate manner without her consent. This took place on Jimmy Kimmel Live! During a 2006 episode, he invited both of them for what was supposed to be a fun and light-hearted evening. Things became rather escalated when Dick asked Trump’s daughter: “You don’t play up the glitter on your legs?” Ivanka responded sternly, “Oh wait, did I say I was single? I thought I had a boyfriend…” Despite the host and Ivanka warning him repeatedly, Dick didn’t bat an eye. As a result, security escorted him off the stage with the host issuing a deep apology. This is definitely one of the most uncomfortable episodes to come across to this day for both Ivanka and viewers. 

4. That 'Common' Thread Between Father and Daughter

Image Source: Getty Images | Photo by Ben Rose
Image Source: Getty Images | Photo by Ben Rose

 

As per a People report, comedian Andy Dick got plenty of backlash after he reportedly touched Ivanka on her thigh in a very inappropriate manner without her consent. This took place on Jimmy Kimmel Live! During a 2006 episode, he invited both of them for what was supposed to be a fun and lighthearted evening. Things escalated when Dick asked Trump’s daughter, “You don’t play up the glitter on your legs?” Ivanka responded sternly, "Oh, wait, did I say I was single? I thought I had a boyfriend." Despite the host and Ivanka warning him repeatedly, Dick didn’t bat an eye. As a result, security escorted him off the stage, with the host issuing a deep apology. This is definitely one of the most uncomfortable episodes to come across to this day for both Ivanka and viewers.

5. When Ivanka Snubbed Her Step-Mom Melania Trump

Image Source: Getty Images | Photo by Kevin Mazur
Image Source: Getty Images | Photo by Kevin Mazur

 

Fairytales have often portrayed the relationship between stepmothers and stepdaughters in a rather twisted tale. There’s almost no story in fables that paints this rather unique relationship in a good light. Coming back to reality, Ivanka and her stepmother, Melania Trump, don’t particularly get along as well as one would hope. Although the two often flaunt bright smiles while next to each other, it appears that things are entirely different between them. According to the Daily Mail, during a 2020 Republican National Convention, a video of Melania rolling her eyes at Ivanka went completely viral. The former Trump campaign advisor was invited on stage by her father when this moment was caught on camera by people in attendance that day. Although the two never really addressed the moment, critics speculate that perhaps they truly gel well with each other. Whether or not that relationship has since changed or remains the same is yet to be known.

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