Donald Trump Jr and his former fiancee, Kimberly Guilfoyle, had a friends-to-lovers story that ended after four years.
US President, Donald Trump's son, Donald Trump Jr., and his fiancée, Bettina Anderson are set to get married this Memorial Day weekend, on May 23–25, 2026. The festivities will reportedly take place in a highly private ceremony on a private island in the Bahamas. The news is all over the internet and is generating immense buzz due to its high-profile nature. The couple initially considered a lavish White House wedding. However, they changed the plans due to current global tensions, specifically the Iran conflict.
Sources shared with Page Six that the Bahamas ceremony will be limited strictly to immediate family and a few longtime acquaintances, due to limited space on the island. Recently, Donald Trump said he might be unable to attend his son's wedding due to geopolitical issues with Iran; however, he will do his best to attend and bless the couple. Notably, it is not Donald Trump Jr's first time being an engaged man. He went down that road twice earlier, with his last fiancée being Kimberly Guilfoyle. Here's everything we know about her and the reason why their relationship went downhill.
Kimberly Guilfoyle is an American attorney, television news personality, and diplomat. According to PEOPLE, she was born on March 9, 1969, in San Francisco. She was brought up in the Mission District by her mother, Mercedes Guilfoyle and father, Anthony Guilfoyle. On her social media, she calls herself a "proud Latina", honouring her mother, who passed away when she was just 10. After her death, Kimberly, according to PEOPLE stated that she remembers growing up "surrounded by love," with her "own personal guardian angel watching over" her. Her mom, Mercedes was from Puerto Rico and her dad, Anthony hailed from Iceland, as per The List.
Kimberly is an orphan as of 2026, as her father tragically died of cancer in 2008. As for her career, she currently serves as the United States Ambassador to Greece. She was formerly a San Francisco prosecutor who steadily worked her way up to the diplomatic ranks. Regarding her academic background, she graduated from UC Davis and studied at the University of San Francisco School of Law, per SFGate. Back in school, she interned at the San Francisco district attorney's office, which later helped her launch a career as a prosecutor, as per PEOPLE.
During her time at law school, Kimberly briefly worked as a model and actress to pay for her tuition. She also pursued a career in broadcasting before opting for a full-time legal course. In 2004, she moved to New York, and signed on to host the Court TV series, Both Sides. Kimberly was hired as a legal analyst for numerous programs, including Good Morning America, Larry King Live and Anderson Cooper 360. She also worked with Fox News from 2006 to July 2018. Thus, besides being Donald Trump Jr's ex-fiancée, she is a multifaceted individual who has built a name for herself in her own right.
Kimberly and Trump Jr have been acquaintances for a long time. After years of remaining friends, they decided to go on a date and to their pleasant surprise, sparks flew, and they started developing romantic feelings for each other. Although the exact date when Trump Jr and Kimberly's relationship began is not publicly known, they were first linked up in April 2018, when paparazzi spotted them out at a dinner date in New York City. Sharing their friends-to-lovers story with Metropolitan Palm Beach magazine, Kimberly stated:
"Don and I knew each other for years but when we went on one date years later, that was it. Sparks. In fact, we have been together from that night on, happily ever after!"
In May 2018, Trump Jr and Kimberly went Instagram official by sharing a couple pic from a Poison rock concert. In the next month, the former couple publicly announced their love on the political stage at the Montana Republican Party's national convention. At that time, Trump Jr gave her a shoutout during his speech. Days later, Kimberly attended her first official White House event by Trump Jr's side during a Fourth of July military families picnic. After about two years of dating, the duo got engaged in a private ceremony on New Year's Eve 2020.
After living as fiancés for four years, Donald Trump Jr and Kimberly Guilfoyle called off their engagement after quietly separating in December 2024. While the duo tried to maintain privacy about the cause of their split, insiders told Page Six that there had been issues in their relationship for over a year. The source also alleged that the former couple frequently argued and even openly bickered in front of people at Mar-a-Lago. Shortly after, he moved on with his now-to-be wife, Bettina Anderson. The insider was quoted as saying:
"Don and Kimberly haven't been getting along over the past year. 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."
What are your thoughts on Donald Trump Jr and Kimberly Guilfoyle's friends-to-lovers story? Let us know.
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