Kimberly Guilfoyle Takes Another Hit In Humiliating Break-Up Saga With Don Jr.

After Donald Trump Jr. and Kimberly Guilfoyle confirmed their split in December 2024, the former couple quickly moved on to other ventures. As Guilfoyle prepared to take on the role of U.S. ambassador to Greece, Don. Jr. focused on his relationship with Bettina Anderson. By December 25, Don Jr. and Anderson were engaged. Despite Donald Trump's somewhat suspicious response of to the news, Don Jr. and Anderson's relationship appears to be going strong. Although they haven't divulged a wedding date, Anderson's bridal shower is scheduled for April 2026, according to Page Six, which indicates the ceremony will likely happen sooner rather than later.

This speedy timeline could be a gut punch for Guilfoyle, since it's pretty much the opposite of her experience with Don Jr. In their case, they got engaged after a couple of years of dating, and it took them another year to publicly announce the news. To make matters worse, after two years of not moving forward, Guilfoyle and Don Jr.'s relationship broke down into a messy, protracted ending. Half a year before he officially broke up with Guilfoyle, Don Jr. was reportedly already involved with Anderson. Their interactions caught public attention, and Guilfoyle had to endure months of gossip.

Given Guilfoyle's chilly response to Don Jr. and Anderson's engagement, it's likely she's not too pleased about the imminent bridal shower. While lots of people are apparently Jonesing to go to the bash, it seems safe to assume that Guilfoyle is glad to be living and working an ocean away.

Although they never made it to the altar, Kimberly Guilfoyle and Donald Trump Jr.'s long relationship gave them plenty of time to do other things, like investing in pricey real estate. In 2021, while they were keeping their engagement on the DL, Guilfoyle and Don Jr. reportedly spent almost $10 million on a home in Florida.

After Don Jr. was engaged to Bettina Anderson, he and his former fiancee were still connected by this property. It took until February 2026 for Guilfoyle and Don Jr. to put their mansion up for sale. While prepping a house for sale can be a lengthy process, part of the delay included some awkward details. "As recently as not that long ago, Kimberly and Don still hadn't completely moved out of each other's places, and Don still had many of his belongings at Kimberly's home, including clothes and shoes," one insider admitted to People in January 2026.

Moving is a hassle at the best of times, and the combo of breakup moving/relocating internationally was reportedly extra stressful for Guilfoyle. "She is worried about the stuff she's leaving behind. The last thing she wants to do is see Bettina using something she owns," another individual confessed to Radar. However, once the home sells, both Guilfoyle and Don Jr. could reap some serious financial rewards. If they can get their hoped-for price, they could triple their initial investment.