Kimberly Guilfoyle Offers a Graceful Blessing for Donald Trump Jr.’s Upcoming Wedding

Donald Trump Jr.’s former fiancée, Kimberly Guilfoyle, has offered her perspective on the businessman’s upcoming marriage to Bettina Anderson.

“I’m pleased for Don,” Guilfoyle, 56, shared in a conversation with The New York Times, as detailed in an article released on Sunday, January 4. “Naturally, I wish him all the best.”

Don Jr., 48, revealed his engagement to Anderson, 40, at a holiday celebration alongside his father, President Donald Trump, at the White House in December 2025.

“She said ‘yes,’ so that’s a significant victory for the end of the year,” he informed guests at the gathering.

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Anderson expressed, “It’s truly been the most memorable weekend of my life, and I’m about to marry the man of my dreams. I feel incredibly fortunate.”

Donald and Anderson were initially linked in December 2024. Their relationship began shortly after Don Jr. and Guilfoyle ended their engagement after six years together.

“Don and Kimberly ended their relationship before the election and began dividing their assets around the end of September,” a source confided to Us Weekly in December 2024.

The source added that Trump and Guilfoyle “did not publicly discuss” their separation to avoid distracting from other “critical matters.”

Don Jr. told Page Six at the time, “Kimberly and I will always cherish each other and will maintain a special connection. I couldn’t be prouder of her and the vital role she’ll continue to play [as U.S. ambassador to Greece].”

Another insider exclusively told Us after Don Jr. and Guilfoyle’s split that while their “partnership had reached its conclusion,” their bond was “genuine.” Meanwhile, the insider noted that Don Jr.’s romance with Anderson is “distinctly different.”

“Regarding his relationship with Bettina, it’s solely focused on them,” the insider continued. “He’s seeking a partner. She doesn’t require anything from him and simply wants to be with him.”

Prior to his split from Guilfoyle, Don Jr. was married to Vanessa Trump from 2005 to 2018. The former couple share daughters Kai, 18, and Chloe, 11, and sons Donald III, 16, Tristan, 14, and Spencer, 13.

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Now, Don Jr. and Anderson are anticipating their next chapter.

“Bettina is overjoyed to be engaged to Don, and they’re already beginning to plan the wedding,” a source exclusively told Us in December 2025. “She has desired this from the beginning and knew he was her ideal match. She appreciates how he has incorporated her into his children’s lives and is such a devoted father.”

The insider added, “The wedding will be scheduled around Don and his dad’s demanding schedules. They want [Donald’s wife, first lady Melania Trump] and Donald to be present and have ample time to enjoy it. … Bettina has been prioritizing her well-being through exercise, skincare treatments, and generally feeling healthy. So she feels confident about walking down the aisle sooner rather than later.”

The source concluded, “Her ring is exquisite and she can’t stop smiling and radiating happiness. Don is her dream man, and the entire family has warmly welcomed her.”