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.

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.

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.

Trump Jr. posted their first Instagram photo together with Bret Michaels of the band Poison. Guilfoyle also shared the image on her profile.

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."

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."

Rosendale lost the 2018 midterm election, and Tester was reelected to a third term in the US Senate.

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.

Trump Jr. and Guilfoyle sat in the front row at a Zang Toi runway show.

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.

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.

"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.

"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!"

Trump Jr. and Guilfoyle — both avid hunters — marked the launch of a coalition called Sportsmen for Trump.

Trump Jr. held the book signing at a Marriott Hotel in Long Island, New York.

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.

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.

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.

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."

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. 

The 11,300-square-foot waterfront estate features six bedrooms and 11 bathrooms, People magazine reported.

"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.

"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."

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.

"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."

"America is Trump country!" Guilfoyle said in her speech.

"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.

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."

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.

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.

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."

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.

San Francisco attorney Art Groza introduced the couple at a fundraiser for John Burton, who was then a member of the California State Assembly and went on to be elected to the House of Representatives, The San Francisco Chronicle reported.

Newsom and Guilfoyle wed at St. Ignatius Church in San Francisco. At the time, Newsom worked as a county supervisor, and Guilfoyle was an assistant district attorney.

Months later, Newsom told the San Francisco Chronicle that living on different coasts had "taken a huge toll personally."

"The transcontinental marriage is tough — the only godsend is that we don't have kids," he said. "You give up your life in the traditional sense."

One image from the Harper's Bazaar spread showed Guilfoyle and Newsom lying together in formalwear on a rug at Ann and Gordon Getty's house.

In the accompanying article, Newsom described their relationship as "a wonderful combination of being in love and extraordinarily proud."

Newsom and Guilfoyle released a joint statement announcing the end of their marriage "with great sadness," The San Francisco Chronicle reported.

"Unfortunately, the demands of our respective careers have made it too difficult for us to continue as a married couple," the statement said. "Over the past 10 years, we have developed a tremendous bond of love and respect for each other. That will never change. We will remain close friends. We ask for your understanding and consideration during this difficult time."

After the two were spotted together at Newsom's birthday party, a golf championship, and an outing with then-Prince Charles and Camilla during their royal visit, The San Francisco Chronicle described their marriage as "on-again, off again."

When former San Francisco mayor Willie Brown asked about his marital status at the royal gathering, Newsom replied, "I have a very confusing life," the Chronicle reported.

Guilfoyle gave a vague answer to the Chronicle when asked if she and Newsom had gotten back together.

"If I was standing back and looking at the situation, I would say it went great — these two people obviously love each other and get along very well," she said. "But I don't have an answer for you. We are not back together."

Guilfoyle told The San Francisco Chronicle that the divorce was amicable, and that she and Newsom shared a lawyer throughout the proceedings.

"We're very close, and we're going to remain that way," she said.

Guilfoyle and Newsom did not have any children together during their marriage.

Villency and Guilfoyle welcomed a son in October 2006. They divorced in November 2009.

After Newsom's campaign manager, Alex Tourk, abruptly resigned for "personal" reasons, Newsom publicly apologized for the affair the next day, the Los Angeles Times reported.

"I want to make it clear that everything you've heard and read is true, and I'm deeply sorry about that," he said at a press conference. "I've hurt someone I care deeply about — Alex Tourk, and his friends and family. And that is something I have to live with."

Newsom and Siebel wed in Stevensville, Montana, on a ranch belonging to Siebel's parents, People magazine reported. Nancy Pelosi, former San Francisco mayor Willie Brown, and actor Jason Lewis were in attendance.

The couple now shares four children.

In a profile of Newsom in The Sacramento Bee, Guilfoyle described him as "an amazing 'ideas guy' in terms of having an idea, developing it and seeing it to fruition."

She also recalled his dedication to an array of small businesses he operated, including wine shops, bars, and cafés. Guilfoyle told The Sacramento Bee that Newsom handled "everything from food selection and menus" to "all of the personnel decisions."

Newsom won the race for California governor in the 2018 midterm elections and took the oath of office in 2019.

Guilfoyle told The Washington Post that she joked with Newsom about directing Trump Jr. to campaign against his bid for governor, and that the two men discussed the hair products they use to keep their styles intact.

"Gav's hair is slicked back, and Don's hair is slicked back," she said.

Newsom told KQED host Lily Jamali that he was "still trying to come to grips with all of it."

"I wish her well, and them well," he said of Guilfoyle and Trump Jr. "And we see the world, clearly, with a different set of eyes politically."

In an interview on PROFILE by BuzzFeed News, Newsom was asked if then-President Trump had ever mentioned Newsom's past marriage to Guilfoyle in their conversations.

"We may have had a private moment on that conversation, which in and of itself, makes life just interesting," Newsom said.

When host Ben Smith asked Newsom for details, he simply said, "Life's interesting."

"If you want to see the Socialist Biden Harris future for our country, just take a look at California," Guilfoyle said in her speech. "It is a place of immense wealth, immeasurable innovation, and immaculate environment, and the Democrats turned it into a land of discarded heroin needles in parks, riots in streets, and blackouts in homes."

Fox News host Elex Michaelson asked the California governor if he had a response. Newsom opted to "respectfully defer to the next question."

When MSNBC host Alex Wagner asked if he and Guilfoyle still spoke, Newsom replied, "Nope. Not lately."

"It must be weird for you," Wagner said.

"Yeah, of course," Newsom replied.

As speculation swirled that Newsom might run for president in 2024 if President Joe Biden didn't seek a second term, Guilfoyle appeared to allude to her past with Newsom in a speech at Turning Points USA.

"In California, they have vowed to get rid of gas-powered cars with no explanation of how they are going to fund and power alternatives," Guilfoyle said. "A bunch of winners over there, folks. Ask me how I know."

"He ain't making it to the White House," she added, seemingly referring to Newsom.

On an episode of CNN's "The Axe Files" podcast, Newsom said Guilfoyle was "spending a lot of time in Democratic circles" while they were married, citing her work for a progressive district attorney and former friendship with fellow California attorney Kamala Harris, who went on to become vice president.

"She fell prey, I think, to the culture at Fox in a deep way," Newsom said of Guilfoyle. "She would disagree with that assessment, she would perhaps suggest that she found the light."

On an episode of "The Charlie Kirk Show" later that week, Guilfoyle called Newsom's comments "absurd," adding that she was a registered Republican while they were married and that it was Newsom who had changed drastically.

"I didn't change, he did," she said. "He used to be so proud to fight for small business, for entrepreneurs, for those hardworking men and women. And he's fallen prey to the left, the radical left, that is pushing him so far to the left that it's unrecognizable."

Guilfoyle also said that she thought Newsom would run for president in 2024 and that it's something he "wants very badly."