Donald Trump's Weird Behavior Involving Bill Gates' Daughter Set His Ex-Wife On Edge

It should come as no surprise that President Donald Trump's skeevy praise of White House Press Secretary Karoline Leavitt wasn't the only instance where he's made inappropriate comments about a woman. In 2018, Microsoft co-founder Bill Gates addressed the divisive politician's strange behavior towards his daughter during a Gates Foundation meeting. Jennifer Gates, who lives a wildly lavish life, had met Trump before he ever ran for office at a Florida horse show. And the real estate mogul turned on the charm to try and impress her. At one point, Trump left the venue, only to return in a helicopter. 

As Bill asserted, "Clearly he had been driven away but he wanted to make a grand entrance," per MS Now. The tech billionaire went on to recall the first time he met the controversial politician, shortly after his 2016 election victory, and how the encounter had been pretty creepy, to say the least. "When I first talked to him, it was actually kind of scary how much he knew about my daughter's appearance. Melinda [Gates' ex-wife] didn't like that too well," he revealed. Jennifer has never publicly commented on their encounter, but the president's disturbing behavior towards women is hardly new. 

During his time as the head of the Miss Universe and Miss USA Organizations, Trump allegedly overstepped his bounds with many of the contestants, with some accusing him of fat-shaming while others alleged that he'd made unwanted advances, like kissing them without their consent. It's no wonder Melinda Gates found the future leader's comments about her daughter's looks uncomfortable, and while she's never directly addressed it, the philanthropist has made it clear that she's definitely not a Trump fan.

Donald Trump's transformation does not impress Melinda Gates. On the contrary, she'd rather watch him leave the White House sooner rather than later. When Trump first became president, Melinda arranged a meeting with him in an attempt to convince him not to cut funding for contraceptives. "I didn't get anywhere. We'll just say that," she informed The Times of the encounter during a 2025 interview. Asked whether she would attempt another sit-down with the controversial politician, as his second term commenced, Melinda bluntly replied, "I don't think there's any reason to right now. I meet with people where I feel like we can make progress on issues." Clearly, the philanthropist doesn't think Trump capable of making progress on much of anything.

Melinda, who has previously admitted to voting for both the Republican and Democratic Parties in the past, made her stance pretty clear while appearing on "CBS Mornings" in June 2024. "I cannot vote for a man who rolls back women's reproductive rights and says the heinous things that he says about women. So, I absolutely am not voting for Trump," she reasoned (via Facebook). During her chat with The Times, Melinda doubled down on her distaste of him, and when she was prompted on whether or not she believes he's a dictator, Melinda replied plainly, "It appears that's what he would like."