The rumors have been swirling for months that Don Jr. and Kimberly Guilfoyle’s relationship was on the rocks.
Awkward public moments, a reported uptick in bickering among friends and family, and whispers of “another girl” were the tell-tale signs that have proven true, after all.
The two haven’t yet announced the breakup or officially called off their engagement.
But with Don Jr. sharing an intimate birthday outing with Palm Beach socialite Bettina Anderson, a birthday card that read, “I think you’re perfect”, and a few snapshots caught of the pair kissing during an intimate dinner outing — official or not, his engagement with Guilfoyle is definitely over.
🚨 Donald Trump Jr. Splits with Kimberly Guilfoyle 🚨
Sources confirm Don Jr. and Kimberly Guilfoyle have broken up after a "rocky" year. Trump Jr. is now dating glamorous Palm Beach socialite Bettina Anderson, with the couple spotted holding hands in Palm Beach. 🏖️… pic.twitter.com/XRl933lCBk— TheGoonyBin (@TheGoonyBin) December 11, 2024
The breakup rumors were starting to run rampant, apparently the result of Guilfoyle and Don Jr’s intention of waiting until after the inauguration before they announced their split.
Here’s a quick synopsis video from Page Six leading up to the confirmation of the split, and Don Jr’s new relationship with Anderson.
After the outing marking Anderson’s 38th birthday celebration, the reality of the situation was hard to cover over.
Anderson’s lavish home is not far from the Trump family’s Mar-a-Lago property, and Don Jr. is reportedly spending a lot of time there according to the Daily Mail.
Her place is only a mile from his father’s sprawling oceanfront Mar-a-Lago Club, set once more to be the Winter White House.
The couple’s lovey-dovey dinner Monday night came after a lavish weekend of celebration for Bettina’s 38th birthday.
It was also on the day she posted a social media picture of birthday flowers, referencing @donaldtrumpjr.
The next president’s son stayed overnight with Anderson on Friday through Saturday after she enjoyed a magnificent birthday dinner that included a bottle of 2013 vintage Salon champagne, which typically costs an eye-watering $1,300.
She posted a social media image of the super-expensive fizz being poured by a waiter, writing ‘S is for Spoiled’.
And in a clear reference to her new beau, she added: ‘How sweet it is to be loved by you’, accompanied by the the James Taylor song. In a further message, she wrote: ‘IYKYK’, meaning, ‘if you know, you know.’
Don Jr sent his new love a card saying ‘I think you’re perfect’ to mark her 38th birthday.
There was also a photo of a birthday cake being presented to her at the table, with a man who appears to be Don Jr., in a jacket and open necked white shirt, next to her taking a picture on his phone.
ADVERTISEMENTPosted on Saturday, Anderson cryptically captioned it: ‘Definitely feeling a year (or 2) older after last night’.
But the piece de resistance of the celebration was undoubtedly an astonishing 19 inch Y-shaped diamond necklace in 18 carat white gold and with more than 100 jewels weighing a total of 28.27 carats.
The model, influencer and philanthropist from a family with impeccable Palm Beach credentials was wearing it at the dinner on Friday night, setting off her red, blue and black outfit.
Hours earlier she posted a photo of the dazzling piece, along with diamond earrings and the tantalizing words: ‘Tonight I’m gonna have myself a real good time’, accompanied by the sounds of Queen’s hit, Don’t Stop Me Now.
The birthday girl’s charity event a day later was just feet away from the Honor Bar where she and Don Jr. were spotted canoodling at a table on August 17 during an intimate lunch date, as exclusively revealed by DailyMail.com.
Here are a few clips from the Daily Mail capturing the pair leaving after her birthday dinner.
Notice the handholding, the chivalry, but also the slight awkwardness as they caught sight of the photographer.
The fact that they weren’t quite ready to make such a big splash with their relationship yet was evident from the look on their faces as the photographs were snapped.
But Anderson is no stranger to being in front of a camera, as she is often seen modeling high luxury jewelry or appearing on magazine covers, according to a report in USA Today.
She often shares pictures from her photoshoots with her 42,000 followers, including her work as the face behind luxury jeweler and designer Hamilton Jewelers.
Anderson also appeared on a 2022 cover of Palm Beach Illustrated to discuss her nonprofit, The Paradise Fund, which aims to “educate and spread awareness about causes of… ongoing changes in weather patterns that ultimately become natural disasters.”
She co-founded the nonprofit with her brothers Kent and Loy in 2005, which provides disaster relief to impacted communities and funding for Florida-based filmmakers to share stories about the importance of conservation efforts.
Anderson is the daughter of late banking mogul Harry Loy Anderson Jr., who became the youngest bank president in U.S. history when he took over Worth Avenue National Bank at just 26 years old.
The new lovebirds weren’t the only two experiencing a little awkwardness from having their photos taken together.
The awkwardness was also increased for Guilfoyle.
News of her appointment to become the next U.S. Ambassador to Greece was breaking almost simultaneously as the news of Don Jr. and Bettina Anderson’s budding relationship really took form.
Trump taps Kimberly Guilfoyle to serve as US ambassador to Greece — after reported split with Don Jr. https://t.co/epkI1waTiH pic.twitter.com/QtaKLtgk0D
— New York Post (@nypost) December 10, 2024
Quite a few jokes started popping up on social media, even as Don Jr. kept it classy, and immediately congratulated Guilfoyle after news of her appointment broke.
One commenter on his post asked asked if Don Jr’s Dad could send her ex to an overseas banishment as well.
Can your dad send my ex overseas, too?
— Among the Wildflowers (@deaflibertarian) December 11, 2024
Guilfoyle was “blindsided” by the images that came out showing her fiancé dining with Anderson — and a source allegedly confirmed that their romantic relationship is definitely over, according to a different Daily Mail story.
President-elect Donald Trump announced on Tuesday that Guilfoyle, 55, will be moving overseas next year as his representative in Athens.
Don Jr., 46, said: ‘I am so proud of Kimberly. She loves America and she always has wanted to serve the country as an Ambassador. She will be an amazing leader for America First.’
Guilfoyle got engaged to Trump’s eldest son on December 31, 2020, but that was not made public until January 2022. The pair had been dating since 2018.
She admitted being ‘blindsided’ when images emerged earlier this fall of her fiancé dining with another woman, Bettina Anderson, 38.
A source confirmed to DailyMail.com on Tuesday: ‘There is no more Kimberly and Don – at least not romantically.
‘Their engagement hasn’t officially been called off yet. They were waiting until after the Inauguration to announce.’
Guilfoyle has not been seen with Don Jr., 46, since November 12.
News Nation has also covered the story, noting that it seems as though both Don Jr. and Guilfoyle are intending to make the official split as amicable as possible.
Guilfoyle and Don Jr. were engaged on New Year’s Even in 2020, but their relationship has been widely rumored to have been shaky for some time.
Here are more details on that from the New York Post.
The president-elect’s 46-year-old son, Donald Trump Jr., popped the question to Guilfoyle on New Year’s Eve 2020, and the couple kept their engagement under wraps for nearly a year.
But insiders revealed earlier Tuesday that Don Jr. and Guilfoyle’s relationship had been on the rocks for some time — with the two hinting at the rift in recent public spats at the incoming president’s West Palm Beach, Fla., resort.
“Don and Kimberly haven’t been getting along over the past year,” one source said. “They get argumentative at Mar-a-Lago in front of people. Nothing crazy, but you know when a couple is fighting. They bicker in public.”
Photos have also emerged of Don Jr. out and about with Palm Beach socialite Bettina Anderson, suggesting that he and Guilfoyle have ended their relationship and engagement.
She married Democratic California Gov. Gavin Newsom in 2001, when he was a San Francisco city supervisor, but the pair divorced in 2006.
As of the time of this writing, neither Guilfoyle nor Don Jr. have spoken openly about their split or Trump’s new love interest.
But as the News Nation host described, Guilfoyle’s appointment to the Greek Ambassadorship will likely give the two all the cover they need to make as little fuss about their failed romance as possible.
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