Kimberly Guilfoyle Refused to Be Seen as a Loser After Don Jr. Dumped Her for Bettina Anderson

Donald Trump Jr. and Bettina Anderson’s relationship reportedly faced behind-the-scenes resistance before their marriage, according to a new report from the Daily Mail. The outlet claimed that Trump Jr.’s former fiancée, Kimberly Guilfoyle, and Anderson’s ex-fiancé, billionaire heir William “Beau” Wrigley, formed an unexpected alliance after learning that Trump Jr. and Anderson were dating. Sources alleged the two discussed the relationship privately and shared concerns that the romance would not last.

The report said the alleged effort took place as both Guilfoyle and Wrigley were dealing with their own breakups. Guilfoyle had ended a long relationship and engagement with Trump Jr., while Wrigley had previously been engaged to Anderson. According to the account, the two were said to have hoped worries about Anderson would spread through Palm Beach social circles and create problems for the couple.

Months later, Guilfoyle and Wrigley were reportedly seen together at a Palm Beach fundraiser at The Breakers, where Wrigley was serving as co-chair. Their appearance together sparked speculation, though sources insisted there was no romance involved. One source quoted in the report said Guilfoyle was determined not to appear defeated and was making an effort to be seen with powerful, wealthy men. The same report also claimed that some Palm Beach society figures criticized Anderson as Trump Jr.’s relationship became more serious, but the couple remained together despite the chatter.

Competing versions of the story emerged. A source close to Anderson dismissed the allegations and called Guilfoyle jealous and petty. A source close to Guilfoyle disputed the idea that she was driving the conversation, saying Wrigley had initiated contact because of concerns based on his past relationship with Anderson and believed Trump Jr. should be aware of them.

Despite the reported drama, Trump Jr. and Anderson moved forward with their relationship. The couple held a civil ceremony in West Palm Beach, Florida, on May 21, followed by a larger wedding celebration in the Bahamas over Memorial Day weekend. Family members attended the festivities, although President Donald Trump did not. He later said official duties in Washington, D.C., prevented him from attending.

After the wedding, Anderson updated her Instagram name to Bettina Trump. Guilfoyle, meanwhile, has continued her political career. In 2024, President Trump nominated the former Fox News personality to serve as U.S. ambassador to Greece, and she was confirmed in 2025.