Donald Trump Jr. and Kimberly Guilfoyle have reportedly broken up after six years of dating.
Trump Jr., President-elect Donald Trump’s oldest son, and Guilfoyle, a Trump campaign advisor and former Fox News host, began dating in 2018. Guilfoyle confirmed their engagement in 2022.
Once called “the prom king and queen of MAGA land,” the pair bolstered Donald Trump’s 2024 presidential run with primetime addresses at the Republican National Convention and appeared at rallies across the US in support of Trump’s campaign.
In December, Trump Jr. was photographed holding hands with Palm Beach socialite Bettina Anderson. He stopped short of confirming that his relationship with Guilfoyle had ended, but said in a statement to Page Six that “Kimberly and I will never stop caring for each other and will always keep a special bond.”
Guilfoyle will remain in the Trump orbit as the president-elect’s pick for ambassador to Greece.
Trump Jr., Guilfoyle, and Anderson did not respond to Business Insider’s requests for comment.
Here’s a timeline of Trump Jr. and Guilfoyle’s relationship.
November 2007: Donald Trump Jr. and Kimberly Guilfoyle ran in the same circles before they started dating.
Guilfoyle and Trump Jr. were photographed together at events in New York City in 2007 and 2008. At the time, they were in other relationships.
Guilfoyle was married to Democratic politician Gavin Newsom from 2001 to 2006, and she was first lady of San Francisco during his time as mayor. After they divorced, she married businessman Eric Villency in 2006 and had a son in 2007. The couple divorced in 2009.
Trump Jr. married model Vanessa Haydon in 2005. They divorced in March 2018 and share five children.
June 2008: They posed for another photo with their then-spouses at an event in New York City.
The Washington Post reported that Guilfoyle and Trump Jr. became friends when her son, Ronan, went to the same private school in Manhattan as his oldest daughter, Kai.
May 2018: Three months after Trump Jr.’s wife Vanessa filed for divorce, Page Six reported that he and Guilfoyle were dating.
Guilfoyle started as a legal analyst at CNN and eventually became a co-host on the Fox News show “The Five.” She left Fox News in 2018 amid reports of sexual harassment, for which the network paid her former assistant a multimillion-dollar settlement, and joined the pro-Trump super PAC America First Action.
Guilfoyle had been connected to the Trump family for years and was in talks to become the White House press secretary, USA Today reported.
Trump Jr. and Guilfoyle began dating in April 2018. That May, Page Six reported that they made their debut as a couple at a send-off party for the Trump administration’s ambassador to Germany, Richard Grenell.
June 2018: They made their relationship Instagram official.
Trump Jr. posted their first Instagram photo together with Bret Michaels of the band Poison. Guilfoyle also shared the image on her profile.
June 2018: Guilfoyle accompanied Trump Jr. to the Montana Republican Convention.
Trump Jr. thanked Guilfoyle in his convention speech as his “significant other,” Vanity Fair reported.
“We’re going to take her fishing tomorrow, then shooting,” he said. “This is a miniature test to see if she really likes it, or if she’s going to pretend to like it, but either way we’re going to have a good time — or at least I will.”
August 2018: Page Six reported that they had nicknamed each other “Pooh Bear” and “Junior Mint.”
Guilfoyle and Trump Jr. were overheard calling each other pet names during a weekend in Southampton, New York, Page Six reported. Guilfoyle reportedly called Trump Jr. “Junior Mint,” which Page Six speculated was a reference to his bank account, and Trump Jr. dubbed Guilfoyle “Pooh Bear.”
September 2018: They returned to Montana to campaign for Matt Rosendale, the Republican challenger of incumbent Democratic Sen. Jon Tester.
Rosendale lost the 2018 midterm election, and Tester was reelected to a third term in the US Senate.
November 2018: Trump Jr. and Guilfoyle walked arm-in-arm at the National Christmas Tree lighting on the National Mall in Washington, DC.
The tree lighting featured performances from Abby Anderson, “The Voice” contestant Spensha Baker, and “American Idol” contestant Gabby Barrett, according to the event’s official website.
February 2019: They attended New York Fashion Week together.
Trump Jr. and Guilfoyle sat in the front row at a Zang Toi runway show.
May 2019: After joining the Trump campaign as a senior advisor in April, Guilfoyle made several appearances at rallies.
Guilfoyle spoke at a rally at the Williamsport Regional Airport in Montoursville, Pennsylvania, in May 2019, and Trump’s 2020 campaign kick-off rally in Orlando that June. She and Trump Jr. were side-by-side at the events.
“She’s definitely made Don Jr. more serious,” R. Couri Hay, a New York publicist, told Business Insider as part of a profile on Guilfoyle. “She’s had years and years on TV. She’s helped guide and train and been very influential in Don’s increasingly very secure, very formidable, very opinionated television personality.”
“They are like the prom king and queen of MAGA land,” a senior Trump advisor told Business Insider.
October 2019: Trump Jr. and Guilfoyle embraced onstage while speaking at the University of Florida.
Trump Jr. and Guilfoyle were paid $50,000 from student activity fees for their appearance, The Washington Post reported. The event drew hundreds of student protesters outside the auditorium.
November 2019: Trump Jr. and Guilfoyle were asked about their marriage plans during a joint appearance on “The View.”
“You and your family have hurt a lot of people and put a lot of people through a lot of pain,” co-host Meghan McCain said to Trump Jr., naming Trump’s attacks on a family whose son was killed while serving in the US Army in Iraq. “Does all of this make you feel good?”
Trump Jr. replied, “I don’t think any of that makes me feel good, but I do think that we got into this because we wanted to do what’s right for America.”
In an attempt to “end on a light note,” co-host Abby Huntsman asked Guilfoyle and Trump Jr. about when they’re getting married.
“Oh my God,” Guilfoyle said, grinning at Trump Jr. and saying they were more focused on getting Trump reelected.
August 2020: Trump Jr. watched Guilfoyle record her heated speech for the Republican National Convention.
“President Trump is the leader who will rebuild the promise of America and ensure that every citizen can realize their American dream!” Guilfoyle said in her RNC speech. “Ladies and gentlemen, leaders and fighters for freedom and liberty and the American dream, the best is yet to come!”
August 2020: They kissed onstage at a rally in Coplay, Pennsylvania.
Trump Jr. and Guilfoyle — both avid hunters — marked the launch of a coalition called Sportsmen for Trump.
October 2020: Guilfoyle joined Trump Jr. for a signing of his self-published book, “Liberal Privilege.”
Trump Jr. held the book signing at a Marriott Hotel in Long Island, New York.
December 2020: Guilfoyle appeared in a Facebook Live video on Trump Jr.’s Facebook page wishing followers a merry Christmas.
As they expressed their gratitude to veterans and members of the military, Trump Jr. also joked on the Facebook Live stream that he was “reasonably thankful for Kimberly.”
He also called Guilfoyle the “voice of reason” who makes sure that his tweets stay in check.
January 2021: They showed some PDA while campaigning before the Senate runoff in Georgia.
Trump Jr. and Guilfoyle kissed during a Republican National Committee Victory Rally at Dalton Regional Airport in Georgia.
Democratic candidates Jon Ossoff and Rev. Raphael Warnock beat respective Republican challengers David Perdue and Kelly Loeffler in the runoff election.
January 2021: Trump Jr. and Guilfoyle skipped President Joe Biden’s inauguration and began looking for homes in Florida.
Trump Jr. and Guilfoyle skipped Biden’s inauguration along with most of the Trump family, instead flying to Mar-a-Lago on Air Force One.
Upon arriving in Palm Beach, the couple began looking for waterfront homes in Admirals Cove, a gated community in Jupiter, Florida, The Palm Beach Post reported. They were reportedly in contracts to buy an $11 million seven-bedroom, 12-bathroom home that featured a wine room, theater, chef’s kitchen, and guest wings. Guilfoyle herself was also looking at the $9.5 million two-story home next door that had six bedrooms and 11 bathrooms.
February 2021: Guilfoyle introduced Trump Jr.’s address at the Conservative Political Action Conference.
Trump Jr.’s speech, titled “Reigniting the Spirit of the American Dream,” covered cancel culture, Liz Cheney, and “the MAGA movement as the future of the Republican Party.”
March 2021: As their search for a Florida property continued, Trump Jr. and Guilfoyle sold their house in the Hamptons for $8 million.
The 9,200-square-foot Bridgehampton home sits on nearly 4 acres in a private gated community. It has seven bedrooms plus a heated outdoor pool, spa, and waterfall.
April 2021: The couple purchased a $9.7 million home in the gated Admirals Cove neighborhood of Jupiter, Florida, about 20 minutes from Mar-a-Lago.
The 11,300-square-foot waterfront estate features six bedrooms and 11 bathrooms, People magazine reported.
January 2022: Guilfoyle posted a photo with Trump Jr. where she appeared to be wearing a diamond ring on her left ring finger, sparking reports that the two had gotten engaged.
“Tonight was extra special celebrating @donaldjtrumpjr’s birthday,” Guilfoyle captioned the Instagram photo. “Don, you are strong, smart, courageous, funny and the love of my life. I can’t wait to spend the rest of our lives together. Love you.”
An unnamed source told The Daily Mail in January 2022 that the pair quietly got engaged on New Year’s Eve in 2020, but neither Trump Jr. nor Guilfoyle had confirmed their engagement publicly.
“Kim has been wearing her engagement ring and both are very excited about blending their families,” a source told People magazine.
February 2022: Guilfoyle confirmed their engagement in an Instagram post calling Trump Jr. her fiancé.
“Falling in love with my fiancé more and more every day,” Guilfoyle wrote in a Valentine’s Day Instagram post. “@donaldjtrumpjr, you’re my best friend, my support system and my forever guy. Happy Valentine’s Day, I love you and can’t wait for the adventures that lie ahead.”
November 2022: Guilfoyle and Trump Jr. attended Trump’s 2024 campaign launch event.
Eric Trump, Lara Trump, and Jared Kushner were also in attendance, but Ivanka Trump skipped the event, saying in a statement that she was stepping back from politics.
December 2022: In an interview with Metropolitan Palm Beach magazine, Guilfoyle said she is “very traditional” in her relationship with Trump Jr.
“I love taking care of Don, the way I saw my mother lovingly take care of my father,” Guilfoyle told Metropolitan Palm Beach magazine. “I go out of my way to make sure he has everything he needs — making coffee in the morning, cooking our favorite meals, doing our families’ laundry, and caring for our home.”
Guilfoyle also said that Trump Jr. loves that she is “traditional yet fiercely independent.”
November 2023: Trump Jr. and Guilfoyle hit the campaign trail for Trump, appearing at a rally in Hialeah, Florida.
“America is Trump country!” Guilfoyle said in her speech.
April 2024: Trump Jr. marked their six-year anniversary on Instagram.
“Thanks for always being there no matter what the haters are throwing our way,” Trump Jr. wrote on Instagram. “I love you.”
The caption was accompanied by photos of Trump Jr. and Guilfoyle engaged in their hobbies of fishing and shooting, as well as a photo of them at the White House.
July 2024: Trump Jr. and Guilfoyle both spoke on the third night of the Republican National Convention.
Guilfoyle delivered a forceful RNC speech, warning viewers that the country is “closer to World War III than any time in my life.”
Trump Jr. was introduced by his daughter, 17-year-old Kai Trump. He praised his father’s bravery after the Pennsylvania shooting, calling him “Trump tough.”
September 2024: Trump Jr. was spotted with Palm Beach socialite Bettina Anderson, sparking speculation that his relationship with Guilfoyle had ended.
In September, the Daily Mail reported that Trump Jr. was seen eating brunch with Bettina Anderson, a model, socialite, and founder and executive director of the wildlife conservation nonprofit Project Paradise. The outlet reported that Anderson was seen kissing Trump Jr. during their meal, raising questions about his relationship status with Guilfoyle.
Anderson did not respond to a request for comment.
November 2024: Trump Jr. and Guilfoyle appeared together at Trump’s election night celebration after he won the race.
Amid rumors about their relationship, Guilfoyle and Trump Jr. continued to appear publicly together. They joined other Trump family members in celebrating Trump’s victory on election night in Palm Beach.
December 2024: The day after Trump Jr. was seen holding hands with Anderson in Palm Beach, Trump announced Guilfoyle as his pick for ambassador to Greece.
Trump Jr. and Anderson were photographed leaving a Palm Beach restaurant while holding hands on Anderson’s birthday, the Daily Mail reported. Anderson also tagged Trump Jr. in a photo on her Instagram story of a bouquet of flowers with a card reading, “Many have said you’re aging out but I think you’re perfect…happy birthday!”
The following day, Donald Trump announced he’d chosen Guilfoyle to serve as ambassador to Greece in his second White House administration.
“For many years, Kimberly has been a close friend and ally,” Trump wrote on Truth Social. “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.”
Trump Jr. congratulated Guilfoyle in a post on X.
“I am so proud of Kimberly,” he wrote. “She loves America and she always has wanted to serve the country as an Ambassador. She will be an amazing leader for America First.”
December 2024: In a statement to Page Six, Trump Jr. did not confirm his breakup with Guilfoyle but said that they “will never stop caring for each other.”
Trump Jr. told Page Six that he and Guilfoyle “will always keep a special bond” and that he “could not be more proud of her and the important role she’ll continue to play in my father’s administration.”
“She’s been an undefeated prosecutor, national TV news star, a leader of the MAGA movement and close advisor to the president,” he added. “The people of Greece are getting an absolute star and now the whole world will see it more than ever.”
Guilfoyle did not share a statement with Page Six and did not respond to Business Insider’s request for comment.
The post Donald Trump Jr. has spoken out on rumors of his breakup with Kimberly Guilfoyle. Here’s a timeline of their relationship. appeared first on Business Insider.
