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Reading: ‘Don Jr. Didn’t Like Kimberly Guilfoyle’s Outfit Choices’ – Insider Exposes the Real Story Behind the Former Couple’s ‘Amicable’ Breakup
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‘Don Jr. Didn’t Like Kimberly Guilfoyle’s Outfit Choices’ – Insider Exposes the Real Story Behind the Former Couple’s ‘Amicable’ Breakup

Published on: September 1, 2025 at 1:22 AM ET

There's more than meets the eye behind the 'amicable' split

Mohar Battacharjee
Written By Mohar Battacharjee
Senior Editor
Kimberly Guilfoyle and Don Jr.'s Breakup Might Have a Messy Backstory
Kimberly Guilfoyle and Don Jr.'s Breakup Might Have a Messy Backstory. Image from @15zanaz/X.com

Netizens were shocked when in December 2024, Donald Trump Jr. and Kimberly Guilfoyle decided to part ways. Though it wasn’t unexpected as breakup rumors had been doing the rounds for some time. Some even speculated Bettina Anderson and Trump Jr.’s connection had a major part in the split. 

That December, one source revealed to US Weekly, “Don and Kimberly broke up before the election and started to divide assets around the end of September.” They mentioned the decision came from Don Jr. first since “they had different goals.”  The person also noted everything was ‘amicable.’  

Donald Trump Jr. and Kimberly Guilfoyle’s whirlwind romance seems to be over! 💔 Is Bettina Anderson the new spark in his life? Share your thoughts on this high-profile breakup!

#DonaldTrumpJr #KimberlyGuilfoyle #BettinaAnderson #CelebrityBreakup #Drama pic.twitter.com/q0bwDWqsFx

— Discernatively (@discernatively) December 23, 2024

 However, a different claim has been in light too. When their breakup news took over the headlines, an insider alleged there was a time overlap. Don Jr. and Bettina Anderson had already been secretly seeing each other for around six months. And surprisingly, Guilfoyle wasn’t unaware of this. The insider told People, “She loves the power and lifestyle.” On the other hand, Trump’s eldest son, wouldn’t shy away to reveal his moments with Bettina and would take her to trips around the country too. The insider had noted, ” Don is smitten with her. Who knows what, if anything, will come from this.” 

Don Jr. first spoke up about their breakup to Page Six. He said, “Kimberly and I will never stop caring for each other and will always keep a special bond.” He even congratulated her for being named as the U.S. ambassador of Greece and declared, “no one deserves this ambassadorship more than she does.” However, no matter how polite they have tried to keep things on the surface, the off-camera scenes might have a different story to tell. 

I am so proud of Kimberly. She loves America and she always has wanted to serve the country as an Ambassador. She will be an amazing leader for America First. pic.twitter.com/S3FjxqCgCx

— Donald Trump Jr. (@DonaldJTrumpJr) December 10, 2024

 Reportedly, Don Jr. wasn’t very fond of her ex’s party girl lifestyle. While speaking to the Daily Mail, an insider noted Guilfoyle had earned the nickname of “Margarita girl.” They further shared, “Don Jr. is a smart guy and very right wing, but he’s not so bothered about power. … But for Kimberly, it’s about power, power, power!” 

Moreover, Trump Junior wasn’t very impressed with her wardrobe choices too. Well yes, that’s a personal choice of course but reports suggest that might have led to tensions between them. According to an insider’s scoop to People, “Don Jr. has been telling people for months that Kim is so uptight and always dresses so professionally in these kinds of dresses and high heels, and never looks relaxed or casual.” 

Some sources are confident that Kimberly Guilfoyle’s outfit choices played a strong role in her split with Don Jr. after four years of engagement. The People source also claimed, “Don Jr. has always wanted to look good in his father’s eyes. Someone like Bettina [Anderson], who is and has been a model, and is in Waspy circles of Palm Beach, is something that [Don Jr. knew] would impress him.”

TAGGED:Bettina AndersonDonald Trump Jr.kimberly guilfoyle
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