scorecardDonald Trump Jr. and Kimberly Guilfoyle have been called 'the prom king and queen of MAGA land.' Here's a timeline of their relationship.
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Donald Trump Jr. and Kimberly Guilfoyle have been called 'the prom king and queen of MAGA land.' Here's a timeline of their relationship.

Talia Lakritz   

Donald Trump Jr. and Kimberly Guilfoyle have been called 'the prom king and queen of MAGA land.' Here's a timeline of their relationship.
Kimberly Guilfoyle and Donald Trump Jr. attend a rally for President Donald Trump in June 2019.Mandel Ngan/Getty Images
  • 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.
  • The couple relocated to Florida after President Trump left the White House.

Donald Trump Jr. and Kimberly Guilfoyle ran in similar circles for years, bumping into each other at exclusive events in New York City with their then-spouses.

It wasn't until 2018 that Guilfoyle, a former Fox News host and ardent Trump supporter, began dating the president's oldest son, turning them into the GOP's premier power couple.

"They are like the prom king and queen of MAGA land," a senior Trump advisor told Insider in October.

Here's a timeline of their relationship.

November 2007: Donald Trump Jr. and Kimberly Guilfoye ran in the same circles before they started dating.

November 2007: Donald Trump Jr. and Kimberly Guilfoye ran in the same circles before they started dating.
Donald Trump Jr. and Vanessa Trump (left) posed with Kimberly Guilfoyle (second from right) at an event in New York City in November 2007.      NEIL RASMUS/Patrick McMullan via Getty Images

Guilfoyle and Trump Jr. were introduced by mutual friends and 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.

June 2008: They posed for another photo with their then spouses at an event in New York City.
Donald Trump Jr. (second from left), Vanessa Trump (middle), Eric Villency (third from left) and Kimberly Guilfoyle (right) in June 2008.      Johnny Nunez/WireImage/Getty Images

According to the Washington Post, Guilfoyle and Trump became friends as 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 Kimberly Guilfoyle were dating.

May 2018: Three months after Trump Jr.
Donald Trump Jr. and Kimberly Guilfoyle.      Steven Ferdman/Getty Images, Astrid Stawiarz/Getty Images for Taoray Wang

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 multi-million dollar settlement, and joined the pro-Trump super PAC America First Policies.

Guilfoyle had been connected to the Trump family for years and was reportedly in talks to become the White House press secretary.

Page Six reported that Trump Jr. and Guilfoyle made their debut at a send-off party for President Trump's ambassador to Germany, Richard Grenell.

June 2018: They made their relationship Instagram official.

June 2018: They made their relationship Instagram official.
Donald Trump Jr. and Kimberly Guilfoye      donaldjtrumpjr/Instagram

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, where they posted more Instagram photos together.

June 2018: Guilfoyle accompanied Trump Jr. to the Montana Republican Convention, where they posted more Instagram photos together.
Donald Trump Jr. and Kimberly Guilfoyle in Montana.      donaldjtrumpjr/Instagram

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."

August 2018: Page Six reported that they had nicknamed each other "Pooh Bear" and "Junior Mint."
Donald Trump Jr. and Kimberly Guilfoyle at a film premiere in August 2018.      Shannon Finney/Getty Images

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 Senator Jon Tester in the 2018 midterms.

September 2018: They returned to Montana to campaign for Matt Rosendale, the Republican challenger of incumbent Democratic Senator Jon Tester in the 2018 midterms.
Donald Trump Jr. and Kimberly Guilfoyle at a campaign rally for Montana Senate candidate Matt Rosendale in Bozeman, Montana, in September 2018.      William Campbell-Corbis via Getty Images

Rosendale lost the 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.

November 2018: Trump Jr. and Guilfoyle walked arm-in-arm at the National Christmas Tree lighting on the National Mall in Washington, DC.
Donald Trump, Jr. and Kimberly Guilfoyle arrive for the lighting of the National Christmas Tree in November 2018.      BRENDAN SMIALOWSKI/AFP via Getty Images

President Trump and Melania Trump presided over the ceremony, which featured performances from Abby Anderson, "The Voice" contestant Spensha Baker, and "American Idol" contestant Gabby Barrett.

February 2019: They attended New York Fashion Week together.

February 2019: They attended New York Fashion Week together.
Donald Trump Jr. and Kimberly Guilfoyle in February 2019.      Theo Wargo/Getty Images for NYFW: The Shows

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.

May 2019: After joining the Trump campaign as a senior advisor in April, Guilfoyle made several appearances at rallies.
Donald Trump Jr. and Kimberly Guilfoyle in May 2019.      Tom Williams/CQ Roll Call

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, Florida, in 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 Insider as part of a profile about 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."

October 2019: Trump Jr. and Guilfoyle embraced onstage while speaking at the University of Florida.

October 2019: Trump Jr. and Guilfoyle embraced onstage while speaking at the University of Florida.
Donald Trump Jr. and Kimberly Guilfoyle speak at the University of Florida in October 2019.      Paul Hennessy/SOPA Images/LightRocket via Getty Images

Trump Jr. and Guilfoyle were paid $50,000 from student activity fees for their appearance, according to the Washington Post. The event drew hundreds of student protesters outside the auditorium.

November 2019: Trump Jr. and Guilfoyle appeared together on "The View," where they sparred with the hosts.

November 2019: Trump Jr. and Guilfoyle appeared together on "The View," where they sparred with the hosts.
Donald Trump Jr. and Kimberly Guilfoyle on "The View" in November 2019.      Photo by Lou Rocco/ABC via Getty Images

"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, naming President 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 President Trump reelected.

July 2020: Guilfoyle tested positive for COVID-19. Trump Jr. tested negative, but canceled scheduled events as a precaution.

July 2020: Guilfoyle tested positive for COVID-19. Trump Jr. tested negative, but canceled scheduled events as a precaution.
Kimberly Guilfoyle speaks at a Make America Great Again campaign rally in Tulsa, Oklahoma, in June 2020.      Win McNamee/Getty Images

Guilfoyle tested positive for the coronavirus after attending two Trump rallies in Tulsa, Oklahoma, and Phoenix, Arizona, both of which had no social distancing or mask requirements.

"After testing positive, Kimberly was immediately isolated to limit any exposure," Sergio Gor, the chief of staff for the Trump Victory Finance Committee, told CNN in July. "She's doing well, and will be retested to ensure the diagnosis is correct since she's asymptomatic, but as a precaution will cancel all upcoming events."

Gor added that Trump Jr. has tested negative for the disease but was self-isolating and also canceling all public events as a precautionary measure.

August 2020: Trump Jr. watched Guilfoyle record her heated speech for the Republican National Convention.

August 2020: Trump Jr. watched Guilfoyle record her heated speech for the Republican National Convention.
Donald Trump Jr. watches Kimberly Guilfoyle as she pre-records her address to the Republican National Convention in August 2020.      Chip Somodevilla/Getty Images

"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 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.

August 2020: They kissed onstage at a rally in Coplay, Pennsylvania.
Donald Trump Jr, and Kimberly Guilfoyle kiss during the Sportsmen for Trump launch in August 2020.      Preston Ehrler/SOPA Images/LightRocket via Getty Images

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 new, self-published book, "Liberal Privilege."

October 2020: Guilfoyle joined Trump Jr. for a signing of his new, self-published book, "Liberal Privilege."
Donald Trump Jr. and Kimberly Guilfoyle at a book signing to promote his book "Liberal Privilege" in October 2020.      Lokman Vural Elibol/Anadolu Agency via Getty Images

Trump Jr. held the book signing at the Marriot 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.

December 2020: Guilfoyle appeared in a Facebook Live video on Trump Jr.
Donald Trump Jr. and Kimberly Guilfoyle snap a selfie.      Paul Morigi/Getty Images

As they expressed their gratitude to veterans and members of the military, Trump Jr. also joked 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.

January 2021: They showed some PDA while campaigning before the Senate runoff in Georgia.
Donald Trump Jr. and Kimberly Guilfoyle campaign in Dalton, Georgia, in January 2021.      Alex Wong/Getty Images

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 Biden's inauguration and began looking for homes in Florida.

January 2021: Trump Jr. and Guilfoyle skipped President Biden
Donald Trump Jr. and Kimberly Guilfoyle exit Air Force One at the Palm Beach International Airport in January 2021.      Noam Galai/Getty Images

Trump Jr. and Guilfoyle skipped President Biden's inauguration along with the rest 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, according to the Palm Beach Post. They were reportedly in contracts to buy an $11 million seven-bedroom, 12-bathroom home that features 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 has six bedrooms and 11 bathrooms.

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