Kimberly Guilfoyle's Ultra-Photoshopped Selfie Hints At Tragic Toll Of Don Jr. Split

Kimberly Guilfoyle's Photoshop habits are often out of control and seem to be getting even more over-the-top. Her March 5, 2025 selfie is so over-edited that the U.S. ambassador to Greece is almost unrecognizable. And, it's easy to wonder if her choice to share this on social media indicates that she isn't handling her split from Donald Trump Jr. as well as it may seem.

Months after the announcement of her breakup with ex-fiancé Don Jr., Guilfoyle took to her Instagram story to share a mirror selfie. In many ways, this selfie is a quintessential Guilfoyle post. She's got the tight minidress, the over-the-top hair extensions, and the typical selfie-ready pout that we've come to expect from her. We have, of course, also come to expect Guilfoyle to do quite a bit of photo editing to her face. Yet, this image seems to be taking her love of Photoshop to new heights. And, it's easy to wonder if Guilfoyle's post was more than just a typical moment of social media sharing. After all, this manipulated photo came the day after Don Jr. and his new partner, Bettina Anderson, rubbed their romance in Guilfoyle's face with some flirty PDA. It's certainly possible that her ex and his new girlfriend getting cozy for the cameras prompted Guilfoyle to attempt her own revenge dress moment. Unfortunately, this attempt may have fallen flat since it's difficult to even recognize her.

Kimberly Guilfoyle and Donald Trump Jr.'s breakup came after months of speculation that he was having an affair with model and socialite Bettina Anderson. After the split, Don Jr. and Anderson wasted no time taking their romance public. No matter the circumstances of the split, this surely stung for Guilfoyle. Then, during President Donald Trump's address to Congress, Anderson and Don Jr. got a bit too close for comfort for a formal, public setting. Anderson was photographed stroking Don Jr.'s face while he appeared to snap selfies. After seeing that, is it a coincidence that Guilfoyle presented an over-edited image of herself to the world? We think not. 

Besides obvious reasons why Don Jr. and Anderson's behavior may bother 55-year-old Guilfoyle, 38-year-old Anderson is nearly two decades her junior. Since Guilfoyle seems to care quite a bit about appearances, this is likely having an effect on her. Furthermore, back in December, an insider told People, "Don Jr. has been telling people for months that Kim is so uptight ... and never looks relaxed or casual," adding, "The tight dresses need to go and she has been told that." Another source noted that Don Jr. dating someone like Anderson was more likely to get his dad's approval. When compounded, this has surely hurt Guilfoyle, and her choice to double down on her often-criticized look certainly sends a message.