It’s no doubt most members of the Trump family are celebrities themselves, a social status that was achieved when Donald Trump made the transition from Page Six-friendly business mogul to bona fide reality TV star in the 2000s.
Now, with Trump back in the White House, the spotlight is shining brighter (and hotter, to be sure) than ever on him and his socialite relatives.
But the Trumps aren’t the only famous faces in their social circle: Over the years, a number of Trump family members have dated celebrities, from sports icons to actors, pop stars, famous models and more.
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The latest in the list of celebrities who have dated Trump family members is none other than golf pro Tiger Woods, who went Instagram official with Donald Trump Jr.’s ex-wife Vanessa Trump on March 24, 2025.
Vanessa was once linked to Leonardo DiCaprio and a Saudi prince before marrying Don Jr. and having five kids, including Kai Trump, who showed up to golf events alongside Woods in early 2025.
Celebrities Romantically Linked to the Trump Family
Did you know Donald Trump once bragged about dating LaToya Jackson, the sister of Michael Jackson and Janet Jackson? More on what she had to say on that accusation, below.
Plus, there was that time Ivanka Trump dated a That ’70s Show star, who was quick to denounce his political affiliation with the controversial family.
From relationships we’re all familiar with such as Melania and Donald, to surprising connections such as Ivanka and Lance Armstrong, you never know what you’re gonna get when it comes to the Trump family dating history.
Celebrities Who Dated Trump Family Members
From pro athletes to pop stars, find out which celebrities have dated members of Donald Trump’s family, from Aubrey O’Day to Topher Grace, Tiger Woods and beyond.
Gallery Credit: Taylor Alexis Heady