Like his father, Donald Trump, Donald Trump Jr. knows a thing or two about divorce. His first wife, model Vanessa Kay Haydon, filed for an uncontested divorce in Manhattan Supreme Court in 2018 after 13 years of marriage and 15 years together.
That same year, while he was still married to Haydon, Trump Jr. started dating Kimberly Ann Guilfoyle, a television news personality and former California prosecutor who served as an advisor and led the fundraising division of Donald Trump’s failed 2020 presidential campaign. It was, in fact, Haydon who confirmed her husband was dating Guilfoyle, telling The Washington Post the news. They got engaged on New Year’s Eve in 2020.
For the most part, the couple has appeared to be a strong unit since getting together six years ago. However, in September 2024, Mail Online ran a story suggesting Trump Jr. was caught kissing glamorous 37-year-old Palm Beach socialite, model, and influencer Bettina Anderson on Aug. 17 during a brunch date at The Honor Bar, located inside Palm Beach’s swanky Royal Poinciana Plaza, with Guilfoyle nowhere to be seen. Onlookers described the pair as being enamored with each other. The story was accompanied by a photograph of them enjoying their food (though no inappropriate romantic canoodling was caught on camera).
Naturally, it has sparked suggestions that Don Jr. and Guilfoyle’s relationship is in trouble or over, with Guilfoyle said to have been “blindsided” by her fiancé’s actions. But is that the case?
Have Donald Trump Jr. and Kimberly Guilfoyle separated?
Despite Donald Trump Jr.’s rendezvous with Bettina Anderson, subsequent rumors about a rift in his relationship with fiancée Kimberly Guilfoyle, and Guilfoyle’s absence from some recent events she was expected to be at with her fiancé, a News Nation source has suggested the couple is “just fine.” The source added, “They have a lot of travel together coming up for the campaign. This is nonsense.”
Another source told the platform, “Bettina and Vanessa (Don Jr.’s ex-wife) are best friends. She’s always at events. Who cares?”
Whether or not anything was going on between Trump Jr. and Anderson is probably immaterial. Members of the Trump family have a history of infidelity without consequence. Just look at the former Cheeto-in-chief, who’s still married to Melania despite reportedly being unfaithful to her countless times — not least in the high-profile case of his one-night sexual encounter with adult movie actress Stormy Daniels in 2006, who Trump paid $130,000 to keep silent about it during his 2016 presidential campaign.
Contrary to our better judgment, we wish Donald Trump Jr. and Kimberly Guilfoyle all the best in their relationship.
