Ivanka Trump was thrust into the spotlight in her teens thanks to her dad Donald Trump, and throughout her multiple careers and marriage to Jared Kushner, the world has watched things get increasingly awkward. Some of her comments and moments in the spotlight – especially those on television – have not been pretty to watch.
Awkward teen among beauty queens
Ivanka Trump made her television debut when she was just 15 years old – she co-hosted her father’s Miss Teen USA beauty pageant in 1997. However, her appearance as a “teen expert” alongside actor J. Eddie Peck didn’t go down very well.
It was clear during her backstage chats with the competitors and while announcing the results that she was “horrendously nervous”, according to the 2019 book Kushner Inc.: Greed. Ambition. Corruption. The Extraordinary Story of Jared Kushner and Ivanka Trump by Vicky Ward.
As well as several slip-ups, Ivanka’s hosting gig was full of embarrassing comments, including an incident after the swimsuit round when she said to the bikini-clad teenagers: “I can guarantee my brothers were loving that. Are any of you single?”
Woody Allen-Soon Yi Previn comparison
On The View in 2006, co-host Star Jones got a shock when she asked The Apprentice star Donald Trump what he’d do if his daughter wanted 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?”
It prompted another co-host Joy Behar to compare Trump to Woody Allen, who infamously married Soon-Yi Previn, the adopted daughter of his former long-term partner Mia Farrow. A Trump spokesman later backtracked, saying the property mogul
was “making fun of himself for his tendency to date younger women”. However, it was still majorly awkward for Ivanka.
Andy Dick’s joke that wasn’t funny
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Comedian Andy Dick got more than a slap on the wrist when he inappropriately touched Ivanka Trump’s legs while on Jimmy Kimmel Live! in 2007 – security dragged him off the stage after he ignored a warning from the host.
When Dick asked Ivanka: “You don’t play up the glitter on your legs?”, she retorted: “Oh wait, did I say I was single? I thought I had a boyfriend.”
In December 2017, the comedian tried to defend his actions in an Instagram post but it was supremely awkward then and it is still difficult to watch now.
Another inappropriate Donald comment
During the “Fave Five” segment on her eponymous daytime TV show, Wendy Williams asked father and daughter what they had most in common. Ivanka answered: “Either real estate or golf.”
Donald could’ve left it at but didn’t. He said: “Well, I was going to say sex, but I can’t relate that to her.” Ivanka squirmed visibly and Wendy hastily moved on to the next question.