Donald Trump Jr. and Kimberly Guilfoyle were once called ‘the prom king and queen of MAGA land.’ Here’s a timeline of their 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 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: 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.”

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.

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.

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: 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.

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.”

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.”

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.”