Donald Trump Jr has been making headlines for all kinds of reasons lately.
But nobody expected him to drop this bombshell at the White House.
And Donald Trump Jr just made one big announcement that left Kimberly Guilfoyle fuming.
President Trump Shares The Happy News With America
President Donald Trump turned a White House Christmas reception into a family celebration Monday night when he announced that his eldest son Donald Trump Jr. was engaged to Palm Beach socialite Bettina Anderson.
The announcement came just one year after the couple first sparked romance rumors in Palm Beach society circles.
Trump Jr. took the podium at the holiday gathering to share his excitement about popping the question.
"I'm not usually at a loss for words, because I'm usually doing the ranting and raving really well," Trump Jr. told the crowd of guests.¹
The 47-year-old businessman and podcast host thanked Anderson for accepting his proposal before describing how nerve-wracking it was to ask the big question.
"When you go down there, it's like, you're gonna go, and you're trying to ask, and you're not sure what the answer's gonna be," Trump Jr. explained. "It's always a little bit rough. But she said yes, which is a big win for the end of the year."²
Anderson wore a sparkling red dress for the occasion and took the microphone to express her joy about the engagement.
"This has been the most unforgettable weekend," Anderson said. "I get to marry the love of my life, and I feel like the luckiest girl in the world."³
The engagement marks Trump Jr.'s third trip down the aisle and comes less than a year after his very public split from former fiancée Kimberly Guilfoyle, who used to be married to California’s Democrat governor Gavin Newsom.
Palm Beach Power Couple Raises Eyebrows
The whirlwind romance between Trump Jr. and Anderson has been the talk of Palm Beach social circles for months.
The couple was first photographed holding hands during a birthday outing in Palm Beach last December, though neither confirmed their relationship at the time.
Anderson comes from one of Palm Beach's most prominent families.
Her late father Harry Loy Anderson Jr. made history as the youngest bank president in the United States when he took over Worth Avenue National Bank at age 26 in 1970.⁴
Her mother Inger Anderson is a well-known philanthropist and business owner who operates Palm Beach Groves, an orange orchard and souvenir shop the couple purchased in 1978.⁵
The 38-year-old Anderson earned a bachelor's degree in art history from Columbia University in 2009 and built a career as a model and socialite before focusing on philanthropic work.⁶
She serves as a supporter of the Hope for Depression Research Foundation and plays a key role in Project Paradise, a Florida-based conservation initiative.⁷
Anderson also regularly volunteers with the Literacy Coalition of Palm Beach County.⁸
The couple made their relationship increasingly public throughout 2025, attending events together including Trump's inauguration in January and traveling to India for a destination wedding in Udaipur.
The Ghost Of Engagements Past
The timing of Trump Jr.'s engagement announcement couldn't have been more awkward for his former fiancée Kimberly Guilfoyle.
Trump Jr. and Guilfoyle dated for six years after getting together in 2018 following his divorce from Vanessa Trump.
They got engaged on New Year's Eve 2020 but didn't make the news public until 2022.⁹
By late 2024, rumors were swirling that the relationship was over after Trump Jr. was spotted getting cozy with Anderson at various Palm Beach locations.
The Daily Mail published photos in August 2024 showing Trump Jr. and Anderson kissing during a brunch date, though he was still publicly engaged to Guilfoyle at the time.¹⁰
Sources told Page Six the couple had "been together for a few months" and were "super cute and happy together" by December 2024 when news of the split finally broke.¹¹
Trump Jr. released a statement to Page Six saying he and Guilfoyle would "never stop caring for each other and will always keep a special bond."¹²
Just days later, President-elect Trump nominated Guilfoyle to serve as U.S. Ambassador to Greece, effectively sending her thousands of miles away from Palm Beach and the Trump family orbit.
The Senate confirmed her appointment in September 2025, and Guilfoyle is now residing in Athens at the official ambassadorial residence known as Jefferson House.¹³
Guilfoyle even joked about finding a "new husband" during her credential presentation ceremony with Greek President Konstantinos Tasoulas.¹⁴
Sources told multiple outlets that the Trump family, particularly Melania and Ivanka, were never thrilled with Guilfoyle's presence and her attempts to profit from the family name.
"Don Jr. has always wanted to look good in his father's eyes," an insider told People. "Someone like Bettina, who is and has been a model, and is in Waspy circles of Palm Beach, is something that [Don Jr. knew] would impress him."¹⁵
Trump Jr. shares five children with his ex-wife Vanessa Trump – daughters Kai, 18, and Chloe, 11, and sons Donald III, 16, Tristan, 14, and Spencer, 13.
Vanessa has since moved on with golf legend Tiger Woods and reportedly maintains a friendship with Anderson, making the situation even more complicated.¹⁶
The engagement announcement signals a new chapter for the Trump family as President Trump begins his second term in office.
¹ "Donald Trump Jr. engaged to Bettina Anderson," NDTV, December 16, 2025.
² Ibid.
³ Ibid.
⁴ "9 things to know about Donald Trump Jr.'s fiancée Bettina Anderson," Business Insider, December 16, 2025.
⁵ Ibid.
⁶ Ibid.
⁷ "Who Is Bettina Anderson, Socialite Engaged To Donald Trump's Son," NDTV, December 16, 2025.
⁸ Ibid.
⁹ "Donald Trump Jr. has spoken out on rumors of his breakup with Kimberly Guilfoyle," Yahoo News, December 19, 2024.
¹⁰ "Donald Trump Jr. & Kimberly Guilfoyle's Breakup Might Have Been an Open Secret in Palm Beach Circles," Yahoo Entertainment, December 11, 2024.
¹¹ Ibid.
¹² "Donald Trump Jr. has spoken out on rumors of his breakup with Kimberly Guilfoyle," Yahoo News, December 19, 2024.
¹³ "Kimberly Guilfoyle's New Life Outside the US," Yahoo Entertainment, November 9, 2025.
¹⁴ Ibid.
¹⁵ "One Year Later, The Real Tea On Don Jr. & Kimberly Guilfoyle's Breakup Is Leaking Out," Nicki Swift, September 1, 2025.
¹⁶ "9 things to know about Donald Trump Jr.'s fiancée Bettina Anderson," Business Insider, December 16, 2025.
