Donald Trump Jr.’s recent engagement to socialite Bettina Anderson has reportedly drawn a skeptical reaction from his former fiancée, Kimberly Guilfoyle. Sources close to Guilfoyle indicate she harbors doubts about the sincerity and long-term viability of the relationship, suggesting Anderson’s motivations may be linked more to the prestige and attention associated with the prominent Trump family name.

Guilfoyle, 56, who ended her six-year relationship with Trump Jr., 47, in 2024, reportedly believes that Anderson, 39, is not “well suited” for her ex-fiancé. An individual quoted by People magazine stated that Guilfoyle finds it challenging to encounter headlines about the new couple, as she does not perceive their union as one built to endure, questioning Anderson’s genuine affection for Trump Jr. beyond the family’s influence.

The public narrative surrounding Trump Jr. and Guilfoyle’s separation claimed an amicable parting. However, reports suggest a more complex timeline, with sources indicating that Trump Jr. had already begun introducing Bettina Anderson as his girlfriend months before the formal conclusion of his relationship with Guilfoyle. This overlap raises questions about the nature of their amicable split.

Further details emerging from insiders suggest that Trump Jr. was keen to impress his father, former President Donald Trump, with his choice of partner. Bettina Anderson, described as a model from “Waspy circles of Palm Beach,” reportedly aligns with the type of individual Trump Sr. would find impressive, potentially influencing Trump Jr.’s relationship choices.

Anderson, daughter of Harry Loy Anderson Jr., who achieved distinction as the youngest bank president in the United States at 26, reportedly faced initial difficulties adapting to the Trump family’s expectations. However, she eventually learned to navigate their social environment, with sources suggesting she adopted a demeanor consistent with the family’s public image, characterized by grace and deference.

The engagement itself was publicly announced by former President Donald Trump during a White House Christmas Party, where Donald Trump Jr. effusively praised his fiancée and expressed gratitude for her acceptance of his proposal. This public display contrasted with alleged private criticisms Trump Jr. leveled against Guilfoyle during their own relationship, particularly concerning her professional fashion sense.

One reported point of contention during Guilfoyle’s relationship with Trump Jr. was his purported disapproval of her attire. Sources claimed he frequently commented on her preference for professional dresses and high heels, suggesting she appeared “uptight” and never “relaxed or casual.” These remarks reportedly included directives for her to alter her fashion choices.

Following the 2024 presidential election, Kimberly Guilfoyle received a significant diplomatic appointment, nominated by President Trump to serve as the U.S. Ambassador to Greece, a role she was confirmed for by the Senate a year later. This appointment came despite the personal complexities of her recent split from the former president’s son.

However, sources close to the situation have suggested that the ambassadorship may have served a dual purpose beyond mere recognition of Guilfoyle’s qualifications. Insiders alleged that the Trump family sought to “send Kim abroad” as a strategic move to manage the aftermath of the breakup, aiming to prevent any potential fallout from impacting Donald Trump Sr.’s political standing, particularly ahead of the election.

The dynamic between the Trumps and Guilfoyle also extended to her previous marriage. Authors Anna Palmer and Jake Sherman, in their book “The Hill to Die On,” recounted an instance where Donald Trump Sr. made an awkward joke at a 2024 fundraising event, referencing Guilfoyle’s ex-husband, California Governor Gavin Newsom, one of the former president’s political adversaries.

During the event, while criticizing Newsom’s policies, Trump Sr. reportedly turned to Guilfoyle and quipped, “Kimberley, you know him, right?” This remark, intended as a jab, was met with “awkward, tepid laughter,” according to the authors, highlighting the unconventional nature of the family’s public interactions.

The Independent has sought comments from both Donald Trump Jr. and Kimberly Guilfoyle regarding the details surrounding these reports, though no official statements have been released on the matter.

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Keywords: Donald Trump Jr. engagement, Kimberly Guilfoyle reaction, Bettina Anderson, Trump family relationships, US Ambassador Greece, Trump Jr. breakup, Gavin Newsom Trump, Political appointments Trump