Eyebrow-Raising Things Donald Trump Has Said About His Daughter Ivanka

Donald Trump may have a positive relationship with all his children, but one reportedly stands above the rest. It has been long conjectured that Ivanka Trump is the former president's favorite child. "When he is talking about Ivanka versus any of his other children, it's just night and day," biographer Marc Fisher said in the documentary "Unprecedented," as noted by Business Insider. "There is a softness, a gentleness, humane aspect to Donald Trump that we never see under any other conditions."

But we have seen much more than softness in how Donald has referred to Ivanka. Starting when she was a teenager, the 2024 presidential candidate has repeatedly been accused of making lewd comments about his daughter. His many guest appearances on "The Howard Stern Show" offer plenty of evidence of his willingness to discuss Ivanka's physique and to allow others to use sexist expressions to refer to her. Stormy Daniels and some of Donald's White House staffers have also accused Donald of crossing the line.

Daniels even said it under oath, though her testimony wasn't as damning as the accusations from one of his former chiefs of staff. But Ivanka's relationship with her father has always been important to her. "There's no doubting my father values beauty, but in my formative years, I never thought he valued it to the point that it should make me uncomfortable," she told Harper's Bazaar in 2007. Ivanka may claim Donald's sexual remarks never bothered her, but they have raised eyebrows across the country and beyond. 

Donald Trump has no issues with others referring to his daughter using derogatory language. He proved that during an interview on "The Howard Stern Show" in September 2004, when the radio host turned the conversation toward Ivanka Trump, who was 22 at the time. Donald felt comfortable enough to jump into the conversation right away. "My daughter is beautiful, Ivanka," he said. Stern agreed, interjecting: "By the way, your daughter ... Can I say this? A piece of a**," he said. Donald responded with "Yeah."

The interview resurfaced amid Donald's first presidential bid in 2016. HuffPost tweeted a story about it, which Ivanka liked from her account, according to CBS News. She later unliked the tweet. "A simple mistake was made by a staff member," an insider said. That wasn't the only time Donald had discussed Ivanka's physique on Stern's show. In October 2006, Stern once again brought up Ivanka's body, asking if she had gotten a boob job. 

Donald denied it, claiming that's how Ivanka was built. "She's actually always been very voluptuous," Trump said. "She's tall, she's almost 6 feet tall and she's been, she's an amazing beauty." In 2003, he also complimented his daughter's body on Stern's show. "You know who's one of the great beauties of the world, according to everybody? And I helped create her. Ivanka. My daughter, Ivanka. She's 6 feet tall, she's got the best body," he told Stern, according to Politico.

Donald Trump reportedly didn't wait for Ivanka Trump to come of age to start talking about her beauty. In August 1997, Ivanka co-hosted the Miss Teen USA event (seen above) while her father, then-owner of the pageant, watched in the audience next to then-Miss Universe Brook Antoinette Mahealani Lee. At one point, he is said to have turned to Lee to ask her opinion regarding Ivanka's looks. "Don't you think my daughter's hot? She's hot, right?" Lee recalled him saying to The New York Times in 2016.

She was put off by Donald's question. "I was like, 'Really?' That's just weird. She was 16. That's creepy," she said. Ivanka was initially disturbed by the article but questioned its veracity. "I was bothered by it, but it's largely been discredited since," she said in a May 2018 interview on "CBS Mornings." Ivanka was referring to a CNN interview in which Rowanne Brewer Lane, an old girlfriend of Donald's who was also featured in the article, stated she had been misquoted.

Ivanka went on to defend her father's treatment of women. "He's not a groper," she said. "It's not who he is. And I've known my father, obviously, my whole life." Donald also responded to the article through a series of tweets. "The failing @nytimes wrote yet another hit piece on me. All are impressed with how nicely I have treated women, they found nothing. A joke!" he wrote in one. 

More than a decade before Donald Trump was found guilty in connection with a hush-money payment to Stormy Daniels, the adult film star opened up about the alleged affair. InTouch initially shelved the 2011 interview after Donald threatened to sue, but it published the story in full in March 2018, two months after The Wall Street Journal broke the news about the $130,000 Donald allegedly paid Daniels. In the bombshell interview, Daniels revealed that Donald once compared her to Ivanka Trump.

Daniels was actually flattered. "He told me once that I was someone to be reckoned with, beautiful and smart just like his daughter. She is smart and beautiful, so I guess that's a compliment," she said. Daniels highlighted that Donald's love for Ivanka seemed genuine, noting she was the only member of his family he ever mentioned in her presence. "He bragged about his daughter quite a bit though. He was very proud of her, which is nice ... But as far as family, that's all he ever said," she detailed.

During the hush-money trial, Daniels reaffirmed Donald told her she reminded him of his daughter. For what it's worth – Ivanka shared a cryptic quote after Daniels' testimony, which many interpreted as a response.

Donald Trump has publicly claimed he would be interested in dating Ivanka Trump if genetics weren't in the way. In 2006, he suggested he would have no issues if his daughter ever posed for Playboy magazine because she has the body for it. "I don't think Ivanka would do that, although she does have a very nice figure. I've said if Ivanka weren't my daughter, perhaps I'd be dating her," he said on "The View."

The co-hosts reacted accordingly. "Stop it! Oh, it's so weird!" one exclaimed, while another could be heard saying: "You know what, you are sick!" Donald laughed, while Ivanka smiled uncomfortably next to him. They continued questioning his answer while he tried to play it down. "Who are you, Woody Allen?" Joy Behar chimed in, referring to the filmmaker's controversial marriage to his ex-wife's daughter. Donald later defended himself, explaining he was making a self-deprecating joke.

"He was making fun of himself for his tendency to date younger women," his rep told Today. "It's a sense of humor that people don't see [from him] all the time." But he went on to make a similar assertion after becoming a presidential candidate in the 2016 election. In an October 2015 Rolling Stone profile, he suggested he would date Ivanka after journalist Paul Solotaroff praised her. "She's really something, and what a beauty, that one. If I weren't happily married and, ya know, her father," Donald said.

To some of his former staffers, Donald Trump's comments about Ivanka Trump weren't jokes. During his presidency, Donald reportedly discussed her physical attributes and even fantasized about her to whoever wanted to hear. "Aides said he talked about Ivanka Trump's breasts, her backside, and what it might be like to have sex with her," former chief of staff at the Department of Homeland Security Miles Taylor wrote in his 2023 book, "Blowback: A Warning to Save Democracy from the Next Trump."

According to Taylor, former White House chief of staff John Kelly – who resigned in December 2018 – had to remind the then-president that it was his daughter he was referring to. "Afterward, Kelly retold that story to me in visible disgust. Trump, he said, was 'a very, very evil man,'" he wrote. Donald has taken shots at Taylor, who gained notoriety after admitting he was the anonymous author behind the 2018 New York Times op-ed titled "I Am Part of the Resistance Inside the Trump Administration."

In 2021, Donald downplayed the role Taylor had in his administration, suggesting his intel is flimsy. "A guy named Miles Taylor, who I have no idea who he is, don't remember ever meeting him or having a conversation with, gets more publicity pretending he was in the inner circle of our Administration when he was definitely not," he said in a statement shared on X.