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Politics
Talia Lakritz
Updated
- Donald Trump Jr. and Kimberly Guilfoyle began dating in 2018 and became a GOP power couple.
- Guilfoyle, a former Fox News host, was a senior Trump campaign advisor and fundraiser.
- Guilfoyle confirmed her engagement to Trump Jr. in an Instagram post on Valentine's Day in 2022.
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Once called "the prom king and queen of MAGA land," Donald Trump Jr. and Kimberly Guilfoyle bolstered Donald Trump's 2024 presidential run with primetime addresses at the Republican National Conventionon Wednesday.
The couple, who began dating in 2018, confirmed their engagement in 2022.
Here's a timeline of their relationship.
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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.
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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 Policies.
Guilfoyle had been connected to the Trump family for years and was in talks to become the White House press secretary, USA Today reported.
Page Six reported that Trump Jr. and Guilfoyle 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.
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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."
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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.
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February 2019: They attended New York Fashion Week together.
Trump Jr. and Guilfoyle sat in the front row at a Zang Toi runway show.
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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.
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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.
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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 McCainsaid 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.
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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.
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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.
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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.
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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 challengersDavid Perdue and Kelly Loeffler in the runoff election.
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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.
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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.
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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.
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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.
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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.
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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 toldMetropolitan 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.
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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, and praised Trump's bravery after the Pennsylvania shooting, calling him "Trump tough."
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