Don Jr thinks Bettina Anderson’s style would win dad’s approval over Kimberly Guilfoyle’s fashion: Source

Don Jr reportedly expressed dissatisfaction with fiancee Kimberly Guilfoyle’s style, feeling it doesn’t align with the Trump family’s image
Frustrated with Kimberly Guilfoyle’s formal fashion, Don Jr reportedly prefers Bettina Anderson’s style for gaining his father’s approval (Getty Images)
Frustrated with Kimberly Guilfoyle’s formal fashion, Don Jr reportedly prefers Bettina Anderson’s style for gaining his father’s approval (Getty Images)

NEW YORK CITY, NEW YORK: Donald Trump Jr's rumored relationship with Palm Beach socialite Bettina Anderson has reportedly raised eyebrows within his family circle.

Sources say the former president’s eldest son believes Anderson, 38, better aligns with the Trump family's image than his longtime fiancee, Kimberly Guilfoyle.

Don Trump Jr sees Bettina Anderson as better fit for his family

PALM BEACH, FLORIDA - MARCH 03: Bettina Anderson attends the Daily Front Row 20th Anniversary Palm Beach, sponsored by Zacapa No. 23 Rum on March 3, 2022 in Palm Beach, Florida. (Photo by Alexander Tamargo/Getty Images for Zacapa No. 23 Rum)
Bettina Anderson attends the Daily Front Row 20th Anniversary Palm Beach, sponsored by Zacapa No. 23 Rum on March 3, 2022, in Palm Beach, Florida (Alexander Tamargo/Getty Images)

Don Jr, 46, and Bettina Anderson were spotted holding hands recently, fueling speculation about the state of his engagement to Kimberly Guilfoyle, 55. A source claims the pair has been dating for about six months, even traveling to Alaska together while Don Jr was still publicly committed to Guilfoyle.

“Don Jr has always wanted to look good in his father’s eyes,” a family insider shared. "Someone like Bettina, who is and has been a model, and is in Waspy circles of Palm Beach is something that would impress him.”

Another source alleges that Don Jr has long been dissatisfied with Guilfoyle’s style, calling it too formal and out of step.

“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," a political insider claimed.

Donald Trump Jr and Kimberly Guilfoyle attend the first day of the Republican National Convention at the Fiserv Forum on July 15, 2024, in Milwaukee, Wisconsin (Andrew Harnik/Getty Images)
Donald Trump Jr and Kimberly Guilfoyle attend the first day of the Republican National Convention at the Fiserv Forum on July 15, 2024, in Milwaukee, Wisconsin (Andrew Harnik/Getty Images)

"The tight dresses need to go and she has been told that."

Meanwhile, Guilfoyle, recently nominated as the US ambassador to Greece by President-elect Donald Trump, may be pressured to step away from the family altogether.

Kimberly Guilfoyle poses backstage for Zang Toi fashion show during New York Fashion Week: The Shows at Gallery II at Spring Studios on February 13, 2019 in New York City. (Photo by Theo Wargo/Getty Images for NYFW: The Shows)
Kimberly Guilfoyle poses backstage for Zang Toi fashion show during New York Fashion Week: The Shows at Gallery II at Spring Studios on February 13, 2019 in New York City (Theo Wargo/Getty Images)

"They are trying to send Kim abroad," a source revealed. "They waited for the election to pass but they didn’t want the split to get in the way of anything to hurt Donald in the election."

Social media erupts over Don Jr's desire for Bettina Anderson to impress dad Trump

Reports suggesting Donald Trump Jr sees Bettina Anderson as a better fit for his family dynamic than fiancee Kimberly Guilfoyle have sparked a buzz on Facebook. Social media users are sharing opinions, with many criticizing the rumored motives behind this potential relationship change.

"Of course, he has to impress Daddy," one user wrote, speculating about the influence of Donald Trump on his son's personal life. They added, "But Daddy is keeping this under control, giving her a hall pass to Greece and probably an NDA."

Another user commented, "Like father, like son." 

"Traditional family values’ strikes yet again," one person quipped. 

"Typical shallow man. They’re all shallow," another wrote, while someone else noted, "Shallow as a cheap paper plate, just like his old man."

"Karma will come for both of them," one commenter said, while another remarked, "Trumpism = use them and throw them away. Not the way to treat people."

This article contains remarks made on the Internet by individual people and organizations. MEAWW cannot confirm them independently and does not support claims or opinions being made online

GET BREAKING U.S. NEWS & POLITICAL UPDATES
STRAIGHT TO YOUR INBOX.

MORE STORIES

Calley Means alleged that Susie Wiles withheld support for his efforts to make children’s diets healthier, citing the need for sugar industry money
2026-11-08T04:56:19.000Z
Jessie Liu will examine government representations about the East Potomac Golf Course renovation and the removal of hundreds of trees
2026-11-08T04:14:15.000Z
Donald Trump backed Sen Dan Sullivan as Rep Mary Peltola held a narrow lead, with thousands of ballots uncounted ahead of ranked-choice tabulation
2026-11-08T02:25:12.000Z
President Trump called the impeachment threats extreme extortion and voiced concern over discussions within the Democratic Party
2026-11-07T22:09:43.000Z
Dana White shared a photo of himself at the White House podium on Instagram after President Trump announced the offer and hinted at a new chapter
2026-11-07T21:01:56.000Z
President Trump said he could work with Democrats without insulting them as he faced his final two years with Republicans in the minority
2026-11-07T19:39:36.000Z
Multiple sources said President Trump had pressured the DOJ to pursue criminal cases against those leaking classified information to the media
2026-11-07T17:35:16.000Z
Alaska's Division of Elections said that the information sought by Mary Peltola's campaign was confidential and not required to be released by law
2026-11-07T16:03:45.000Z
Donald Trump subsequently announced that Stephen Miller would replace Susie Wiles as chief of staff, with the transition scheduled for Monday
2026-11-07T07:38:55.000Z
Abdul El-Sayed faced criticism over his response to the Temple Israel synagogue attack, widening divisions with Michigan's Jewish community
2026-11-07T06:16:46.000Z