Most of Donald Trump’s adult children haven’t inherited his political or entrepreneurial spirit, or even his romantic inclinations. As a result, most of the Trump kids have steered clear of getting into significant age-gap relationships. Eric Trump and Ivanka Trump are only about one year apart in age from their respective spouses. Meanwhile, Tiffany Trump is just four years older than her husband, Michael Boulos. And, although there have been several weird rumors about Barron Trump’s love life, he appears to be single at the time of writing (Barron is reportedly the man to watch on the NYU campus, though, and the ladies are loving it). However, there is one Trump sibling who followed in his father’s footsteps and got into an age-gap relationship: Eldest son Donald Trump Jr. 

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After he and Kimberly Guilfoyle finally announced the end of their years-long engagement in December 2024, through a statement shared with Page Six, he started officially dating his rumored mistress, Palm Beach socialite Bettina Anderson, who’s eight years his junior. In September 2024, sources informed the Daily Mail that Don Jr. and the model had been spotted kissing in public in Florida. To make matters worse, onlookers claimed that they weren’t even trying to keep their romance under wraps, even though Don Jr. was apparently still engaged at the time. Although it’s unclear when Anderson first met Don Jr., she sat behind him, Guilfoyle, and other Trump family members at the 2024 Republican National Convention in July. Although it sounds like Don Jr. and Guilfoyle ultimately didn’t end on the best of terms, he still insisted that they remained amicable in their Page Six statement. However, the former Fox News host is having a hard time moving on.

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In January 2025, Kimberly Guilfoyle celebrated her ex-fiancé Donald Trump Jr.’s birthday with an Instagram Story. Although the new U.S. ambassador to Greece could’ve made things significantly less awkward by sending a message privately or writing a simple “Happy Birthday” and leaving it at that, Guilfoyle decided to post a collage featuring photos of them together over the years. Needless to say, Guilfoyle’s birthday post for Don Jr. served as a heartbreaking reminder that she can’t let go. 

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As a result, it was unsurprising when an insider informed People that the former Fox News anchor was keeping her eyes peeled for any sign of Bettina Anderson at Donald Trump’s 2025 inauguration, adding, “She knows how beautiful and well dressed Bettina is, and there is no question that she was hurt when her romance with Don ended.” Meanwhile, another People insider made it pretty obvious that the socialite wasn’t too fond of her partner’s ex either, asserting, “Bettina wants Kim out of the area.”

Likewise, they also claimed that both Don Jr. and Anderson were actively working to get Guilfoyle out of their orbit ASAP. Luckily, her plushy new job aimed to do exactly that. Still, despite all their differences and rumored dislike for each other, the Trump staffer and Anderson may still be able to bond over the fact that they both entered into an age-gap relationship with the same man. After all, Guilfoyle and Don Jr. shared a much bigger age gap than we knew since she’s eight years older than him.

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