It looks like it’s the end of an era for Donald Trump Jr. and Kimberly Guilfoyle, who have reportedly gone their separate ways and ended their four-year engagement. The former couple, who has not publicly confirmed the split, seem to have parted ways months ago even though they kept up appearances during the presidential campaign.
The buzz around their relationship started in mid-September when a Daily Mail source claimed they spotted Donald Jr. getting very cozy with socialite Bettina Anderson over brunch on Aug. 17 in Palm Beach. “They were definitely on a date. They weren’t exactly making out, but the kisses were romantic, and you could tell they were intimate with each other,” the insider revealed. What makes the reported romantic interlude so fascinating is that Donald Jr. and Guilfoyle made an appearance the next day at the MAGA Boat Parade in Palm Beach County.
Outside of official campaign stops, Guilfoyle was often missing at Trump family gatherings, but Anderson was in attendance — this relationship shift reportedly happened in the late summer. A Page Six source confirmed that timeline, noting, “Bettina and Don have been together for a few months, and are super cute and happy together. It’s just a natural fit — everyone is happy for them!” The Daily Mail even snapped PDA shots of the couple leaving the swanky Buccan restaurant on Monday, Dec. 9 after celebrating her 38th birthday.
Adding to the clues that Donald Jr. and Guilfoyle are done for good was her appointment as the ambassador of Greece by President-elect Donald Trump on Tuesday, Dec. 10. Her ex-fiancé gave the news a thumbs up and congratulated her on the position. “I am so proud of Kimberly,” he wrote on X above his father’s announcement. “She loves America, and she always has wanted to serve the country as an Ambassador. She will be an amazing leader for America First.”
It’s unclear if Donald Jr.’s relationship with Anderson overlapped with Guilfoyle, but his new girlfriend was in the Trump fold at the Republican National Convention in mid-July. Anderson sat next to Donald Jr.’s ex-wife, Vanessa, in a row behind Donald Jr. and Guilfoyle. Anderson is besties with Vanessa, per Page Six, so it just goes to show that Donald Jr. has a very tangled web of relationships.
In the end, it might be a better situation for the Trump family, who didn’t exactly give Guilfoyle a warm welcome. Melania and Ivanka Trump reportedly both took issue with her profiting off the family name. “Kimberly Guilfoyle demanded $60,000 just to introduce the president the day of the [Jan. 6] rally, it was things like that that bothered her,” claimed former White House press secretary Stephanie Grisham to MSNBC in January 2023.
Now, Guilfoyle will be a part of Donald Trump’s second administration, but far away from the White House.
Before you go, click here to see the best presidential love stories in U.S. history.
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