At one point, it seemed certain that Donald Trump Jr. and Kimberly Guilfoyle were in line for their happily-ever-after moment. They met due to their shared political interests and involvement in activities tied to the Republican circle. Guilfoyle and Trump Jr. were first publicly linked in May 2018, shortly after the latter’s split from his then-wife, Vanessa Trump.
Their bond grew stronger over the years, as they were seen attending political events together. Kimberly Guilfoyle also played a major role in Donald Trump’s 2020 re-election campaign, working as a senior advisor. During this time, Donald Trump Jr. was constantly spotted by her side at fundraisers and political rallies, and they would also get engaged soon after.
Donald Trump Jr. and Kimberly Guilfoyle are engaged https://t.co/dm86LhDnEX pic.twitter.com/RsJ5ZGXwdq
— Page Six (@PageSix) January 3, 2022
Unfortunately, Guilfoyle and Trump Jr. ended their relationship in 2024. Sources have claimed that the split was amicable and that the duo still had the same respect for one another, committing to staying connected owing to their shared interests and circles.
The reason for the split was never revealed, but it did not deter Kimberly Guilfoyle’s active role in the Donald Trump Administration. The 55-year-old has been nominated as the US Ambassador to Greece by Trump, solidifying her position within the MAGA camp.
While Donald Trump Jr. moved on and began a new relationship with socialite Bettina Anderson, Guilfoyle’s current relationship status seems relatively unclear. Irrespective, it is being said that she has been keeping an eye on her ex in a protective sense.
Donald Trump Jr. and girlfriend Bettina Anderson continue to put their love on display during Donald Trump’s inauguration festivities pic.twitter.com/pKmu2MapCu
— Riley (valiant/courageous) 🇮🇱 (@Amanda340300021) January 21, 2025
That being said, experts have revealed what her engagement ring might have cost back when it was purchased and how much it would fetch in the current market if Kimberly Guilfoyle were to sell it. Mike Fried, CEO of The Diamond Pro, commented on the possibility of her selling it, saying, “Deciding to sell an engagement ring is a highly personal choice.”
He then opined that it wouldn’t be a difficult process, saying, “Reselling a diamond ring isn’t difficult.” However, he then dropped a bomb that the resale value of diamonds is significantly lower than the list price at which they were bought. Fried gave his expert opinion on how much it would’ve cost Donald Trump Jr. and then revealed an estimated resale rate for the ring.
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Diamonds have a resale value that’s significantly less than the initial price tag. (It’s ) between 20% [to] 60% of the original price. Depending on the quality of the diamond, it could have cost $250,000 originally. She could expect to get anywhere from $50,000 to $150,000 (if she were to resell it).”
