A Timeline of Donald Trump Jr. and Kimberly Guilfoyle’s Relationship

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.

 

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.

Donald Trump Jr. (second from left), Vanessa Trump (middle), Eric Villency (third from left) and Kimberly Guilfoyle (right) in June 2008.

 

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.

A split image of Donald Trump Jr. (left) and Kimberly Guilfoyle.

 

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: Guilfoyle accompanied Trump Jr. to the Montana Republican Convention.

Kimberly Guilfoyle in 2018.

 

Kimberly Guilfoyle in 2018.

Win McNamee/Getty Images

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.”

Donald Trump Jr. and Kimberly Guilfoyle at a film premiere in August 2018.

 

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.”

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.

 

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.”

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

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.

 

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.

Kimberly Guilfoyle speaks at a Make America Great Again campaign rally in Tulsa, Oklahoma, in June 2020.

 

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.

December 2020: Guilfoyle appeared in a Facebook Live video on Trump Jr.’s Facebook page wishing followers a merry Christmas.

Donald Trump Jr. and Kimberly Guilfoyle snap a selfie.

 

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: Trump Jr. and Guilfoyle skipped President Biden’s inauguration and began looking for homes in Florida.

Donald Trump Jr. and Kimberly Guilfoyle exit Air Force One at the Palm Beach International Airport in January 2021.

 

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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