It looks like the great MAGA love story of Donald Trump Jr. and Kimberly Guilfoyle has come to an end, with the oldest son of President-elect Donald Trump seen holding hands with his reputed new girlfriend, Palm Beach socialite Bettina Anderson, during a dinner date in her hometown Monday.
Photos of Trump Jr. and Anderson, walking hand-in-hand while leaving a swanky Palm Beach restaurant, offer “incontrovertible proof” that the soon-to-be first son has moved on from Guilfoyle, his long-time fiancée and partner in pro-Donald Trump campaigning, the Daily Mail reported. Trump Jr., 46, has replaced Guilfoyle, 55, with Anderson, known as a 37-year-old “it girl” with a natural style of glamour, the Daily Mail has concluded.
The New York Post also confirmed Tuesday that Trump Jr. and Guilfoyle had split — shortly before the incoming president announced that he had appointed the former Fox News host to serve as ambassador to Greece in his new White House term.
“For many years, Kimberly has been a close friend and ally,” Trump posted on Truth Social Tuesday afternoon, the Post and other outlets reported. “Her extensive experience and leadership in law, media, and politics along with her sharp intellect make her supremely qualified to represent the United States, and safeguard its interests abroad.”
Guilfoyle, also the ex-wife of California Gov. Gavin Newsom, said Tuesday that she was “honored to accept” Trump’s nomination, which requires Senate approval. Trump Jr. added on X: “I am so proud of Kimberly. She loves America and she always has wanted to serve the country as an Ambassador.”
Any suggestion that Trump was sending Guilfoyle abroad to make way for his son’s new romance with Anderson was met with scorn by the president-elect’s spokesperson, Steven Cheung, the New York Times reported. Cheung said such speculation was “sexist.”
Whatever led to Guilfoyle’s appointment, the “loved-up” Trump Jr. and Anderson spent nearly two hours at the Palm Beach restaurant Buccan Monday night, the Daily Mail reported. The restaurant is some three miles from Anderson’s West Palm Beach townhouse, where the two “have been spending days and nights,” the Daily Mail added.
But if Trump Jr. has been staying at Anderson’s place, that means that Guilfoyle could be holing up in the mansion about 20 miles north that she and Trump Jr. purchased together after they moved to Florida in 2021.
Trump Jr. and Guilfoyle announced their “secret” engagement in early 2022, with the former San Francisco first lady sharing an Instagram photo showing her sporting a massive, sparkling diamond on the fourth finger of her left hand. She declared in a caption, “I can’t wait to spend the rest of our lives together.”
Trump Jr. and Guilfoyle began dating in 2018, shortly after Trump Jr.’s first wife, Vanessa, filed for divorce to end their 12-year marriage. Trump Jr. and Vanessa share five children.
As a couple, Trump Jr. and Guilfoyle, a former San Francisco prosecutor, became known as “the prom king and queen of MAGA” politics as they campaigned together around the country on his father’s behalf. At donor events, they also were known for alluding to their playful sex life, while Guilfoyle often liked to introduce herself to the crowd — or appear at Trump’s Jan. 6, 2021 rally preceding the violent attack on the U.S. Capitol — doing a sexy dance.
Now comes the idea that Trump Jr. has ended his once red-hot romance with Guilfoyle. Then again, speculation has been brewing for months that they were no longer a couple. The Daily Mail first reported in September that his “dalliance” with Anderson had become an “open secret” in elite Republican circles in and around ritzy Palm Beach.
The Daily Mail reported that Guilfoyle was said to be coming to terms that her fiancé had been “fooling around” with another woman.
“Kimberly either didn’t know about Bettina — or didn’t want to know,” an insider told The Daily Mail in September. “Did she hear whispers that Don Jr. was fooling around with someone else? Probably.”
At the time, the Daily Mail also revealed that Trump Jr. and Anderson had been seen “canoodling” and “kissing” during an “intimate brunch” in August.
Breakup speculation grew on on election night, when Trump defeated Vice President Kamala Harris. Trump family observers noted a physical distance between Guilfoyle and Trump Jr., as they joined the rest of the family and other top supporters on stage in Florida to celebrate Trump’s return to the White House.
Trump Jr. could even be seen in video, trying to avoid standing next to Guilfoyle several times before finally settling on turning his back on her, the Daily Beast reported.
But Trump Jr. wasn’t the only person who may have been trying to avoid Guilfoyle that night, according to another Daily Beast report. She seemed to be getting “major side-eye” from Trump Jr.’s oldest daughter, Kai Trump.
Though just 17, Kai has emerged as an enthusiastic MAGA influencer and leading voice in the young, up-and-coming generation of America’s new ruling dynasty. She’s also created a major presence on social media by sharing slickly produced photos and videos about the fun she has hanging out with her beloved, president-elect “grandpa.”
In those posts, Kai has given off major signals as to who’s in and who’s out in the family’s inner circle, according to the Daily Beast. From Kai’s perspective, Guilfoyle looked to be on the outs with the “side-eye” she appeared to give her. If GuIlfoyle hasn’t “won her would-be stepdaughter over, it could be an uphill battle for her future as Mrs. Don Jr.,” the Daily Beast said.
Two days later, Kai Trump posted a curious family photo on X — that didn’t include Guilfoyle. The photo was taken at Trump’s Mar-a-Lago Palm Beach resort on election night, and the teenager captioned it “the whole squad.” The photo showed the future 47th president surrounded by all five of his adult children and three of their partners, along with Kai and her four siblings.
But Guilfoyle was notably absent from the “squad” photo. More or less in her place was Vanessa Trump, who stood with her ex-husband and their five children.
Speaking of Vanessa Trump, Anderson bears some resemblance to her, with both women sporting slender model looks and long, light-colored hair. Anderson often posts photos of herself modeling designer outfits in glamorous settings. She cheekily refers to herself on Instagram as “Your typical stay at home mom … only I don’t do household chores… or have a husband… or have kids.”
Anderson and Vanessa Trump also appeared to be pretty friendly when the socialite attended an “intimate” gathering of Trump supporters in Jupiter, Florida over the summer, the Daily Mail said in another report. Photos and videos shared on social media showed Anderson sitting close to both Trump Jr. and Vanessa Trump. Kai Trump also was seen in the background, sharing a hug with her father and chatting with her mother and with Anderson.
Again, Guilfoyle didn’t appear in any of these images. The Daily Mail reported Tuesday that Guilfoyle has not been photographed with Trump Jr. since Nov. 12.
Meanwhile, Trump Jr. and Anderson looked very much like an established couple while leaving the restaurant in Palm Beach Monday night, according to the Daily Mail. They left the restaurant with another couple, and Trump Jr. could be heard laughing before he and Anderson said goodbye to the others and headed across the street to his pickup truck, while still holding hands.
The first report about Trump Jr.’s alleged romance with Anderson came about four months after he proclaimed his love for Guilfoyle as the couple marked six years together.
“Happy 6 year anniversary @kimberlyguilfoyle thanks for always being there no matter what the haters are throwing our way. I love you,” Trump Jr. gushed in an Instagram post.
To mark the occasion, Guilfoyle also wrote on Instagram: “You are my best friend and my soulmate. Here’s to us and out incredibly blessed life we share together. Looking forward to creating new memories and enjoying more adventures together.”
