Donald Trump Jr.’s love triangle: From Kimberly to Bettina, a tale of two-timing and a breakup

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Donald Trump Jr. is reportedly dating socialite Bettina Anderson after splitting with Kimberly Guilfoyle in April 2024. The breakup and new relationship haven’t been officially confirmed. Both women are set to attend Donald Trump Sr.’s second inauguration. Guilfoyle was appointed as Ambassador to Greece following the split.

It’s all but confirmed. Donald Trump Jr is in a relationship with socialite Bettina Anderson and while the duo haven’t made it official, the two were spotted kissing in Palm Beach and making frequent public appearances together. Trump Jr was earlier engaged to Fox News host Kimberly Guilfoyle whom he started dating in 2018; the couple even purchased a house together in 2021 but reportedly split in 2024 around Easter, according to reports. Now, a Daily Mail report reveals that Donald Trump’s second inauguration is set to be attended by both his son’s ex-fiancée and his current girlfriend, which may make things a bit awkward for Trump Jr.

There has been no official confirmation regarding the broken engagement or the new relationship as of yet.

Around the time when Trump Jr and Anderson went public with their romance, Guilfoyle’s name was announced as Ambassador to Greece. It has been speculated that the move was strategic to send Guilfoyle far away to Greece and to clear the way for Trump Jr and Anderson’s blossoming romance.

While the reports of a budding romance between Anderson and Trump Jr came much later, it is reported that the two started dating at least 6 months before things started coming out in open. Don Jr reportedly took Anderson to Alaska and introduced the 39-year-old socialite as his girlfriend. One of Guilfoyle’s friend felt Anderson had an inkling of what’s happening, but decided to ignore. “She’s no fool but it’s easy to deceive yourself when you’re so committed to someone and believe he’s committed to you.”

Bettina Anderson is a model and social media influencer. She has a huge Instagram following, and describes herself as “a typical stay at home mom”. A face of luxury jeweler and designer Hamilton Jewelers, she also appeared on the cover of Palm Beach Illustrated along with Kent Anderson, and, Samantha Cerny Anderson.

Kimberley Guilfoyle is an alumnus of University of California, Davis, and the University of San Francisco School of Law, became a prosecuting attorney in San Francisco and Los Angeles, California. She was an assistant district attorney in San Francisco from 2000 to 2004. She was raised by her father after she lost her mother Mercedes, who taught special education, to leukemia, at the age of 11. Her father, Anthony “Tony” Guilfoyle who was from Ireland, moved to the US in 1957 at the age of 20. She was married to Gavin Newsom, former mayor of San Francisco, and later to Eric Villency, a furniture heir.

Guilfoyle started dating Trump’s eldest son, Donald Trump Jr. in 2018 and the two got engaged in 2020. However, the duo are rumoured to have split after Trump Jr is said to be seeing Florida socialite Bettina Anderson. In 2021, the couple purchased a home together in Jupiter, Florida. Trump Jr was married to former model Vanessa Trump from 2005 to 2018 and they have five children together – Kai Madison Trump, Donald Trump III, Tristan Trump, Spencer Trump and Chloe Trump.

All seemed to be fine when Donald Trump Jr. had posted an anniversary message for Guilfoyle on April 24, 2024 on Insta. “Happy 6 year anniversary @kimberlyguilfoyle thanks for always being there no matter what the haters are throwing our way. I love you.”

As per sources, Don Jr may have broken up with Guilfoyle to look good in his father’s eyes as he disapproved of Guilfoyle’s style which included tight dresses. He felt that Anderson with her honey-blonde hair and ‘waspy’ model looks, would impress his father.

“Don Jr. has always wanted to look good in his father’s eyes,” the political source told People.

It remains to be seen how Donald Trump Jr manages the presence of both women in his life at his father’s inauguration ceremony.

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