Kimberly Guilfoyle is the new ambassador to Greece, and while everyone is wondering why, there are also questions about her relationship with her fiance Donald Trump Jr. Or her ex-fiance?
For better or for worse (in this case, worse), when a politician is voted into office, the world gets to know their family members. From whether Guilfoyle is still part of the Trump circle to whether the pair split up, it seems like every day, there is more potential drama to unpack. Let’s talk about it and examine their relationship timeline.
Did Donald Trump Jr. and Kimberly Guilfoyle break up?
Don Jr. and Guilfoyle broke up recently, although they haven’t shared the exact date publicly. According to the Daily Mail, the couple celebrated six years together in April 2024. Don Jr. wrote on Instagram, “Thanks for always being there no matter what the haters are throwing our way, I love you.”
Well, did the haters get the best of them? Before diving into what is known about their breakup, let’s talk about the beginning. The former couple knew each other in 2007, although it’s possible they met before then. There are photos of them in 2007 and 2008. They started dating in May 2018, shared the news on Instagram in June 2018, and continued to travel for political events (and New York Fashion Week in Feb. 2019 because they’re both so stylish). Also, in case you needed to know, she calls him “Junior Mint” and his nickname for her is “Pooh Bear.”
Moving on. In 2021, according to Business Insider, Guilfoyle and Don Jr. bought a house in Juniper, Florida for $9.7 million. They got engaged in Jan. 2022 but never got married.
So, here’s a lesson in love from the Trumps (words I never expected to write): if you want to break up with someone, send them out of the country! Most people don’t exactly love running into their exes at Starbucks or the movies, but most people can handle living in the same city or town as someone they used to date. Not Don Jr., apparently. Is Greece far enough? How about the moon?
Does Donald Trump Jr. have a new girlfriend?
But, just in case you were concerned that Don Jr. was lonely now (you were, right?), he seems to be dating a socialite named Bettina Anderson. But maybe Kim is okay with that. She was seen sitting with Matt Gaetz… and the thought of them becoming a couple is even more terrifying than Kim and Don Jr. staying together forever.
Okay, so Guilfoyle and Gaetz aren’t actually dating, but Don Jr. does appear to be smitten with Anderson. A source told People Don Jr. wasn’t a fan of Kimberly’s sense of style and thinks Anderson is going to make his dad happier. The source said his new GF “is in Waspy circles of Palm Beach [which] is something that would impress him.” Nothing more admirable than those Palm Beach Waspy circles! Also, just in case anyone thought Don Jr. was a supportive partner who is not at all stuck in the past, the source told People of Kimberly, “The tight dresses need to go and she has been told that.” I’m not going to say I feel sorry for her, but, um, wow.
Well, Kimberly and her dresses will be in Greece now, and maybe she and Don Jr. will find true happiness without each other. And, according to Alyssa Farrah Griffin, “I want to give credit to my girl” because Guilfoyle “is winning a breakup.” Take that, Don Jr.!