Donald Trump Jr. Hated Ex Kimberly Guilfoyle’s ‘Tight Clothes’ & ‘Uptight’ Demeanor Before Breaking Up With Her For Younger Women

Earlier this week, Donald Trump’s oldest son Donald Trump Jr. was seen in photos holding hands with socialite Bettina Anderson in Palm Beach, Florida, in the wake of the now-public news that he and his former fiancé, Kimberly Guilfoyle, have officially broken up.

Trump Jr. and Anderson are suspected to have been dating for six months.

Although Trump Jr. has not mentioned the separation, he has spent the last stretch of their relationship criticizing her style. A political source close to the family revealed 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… The tight dresses need to go, and she has been told that.”

Photos of Anderson and Trump Jr. kissing in public surfaced last month.

Anderson has reportedly long been pushing Trump Jr. to find a way to move Guilfoyle “out of the area” so as to allow their own relationship to more fully blossom, but Trump Jr. decided not to make any public shifts until after the election to avoid any negative optics for his father.

On Tuesday, Trump announced that he had picked Guilfoyle to serve in Greece as the U.S. ambassador and Trump Jr. jumped on the opportunity to congratulate Guilfoyle.

He wrote in a post on X, “I am so proud of Kimberly. She loves America and always has wanted to serve the country as an Ambassador. She will be an amazing leader for America First.”

Multiple political sources close to the family have explained that Trump Jr. has been specifically looking for a partner who would channel the energy of his late mother, Ivana Trump, and earn his father’s respect.

Many internet users have pointed out the Oedipal complex at play, as Trump Jr. searches for a woman comparable to his mother in order to fulfill his father’s role.

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