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

Somewhere along the way, politics became its own kind of celebrity. And just as Hollywood has its own power couples, both sides of the political aisle are filled with couples that supporters can rally around.

For GOP and Trump supporters, one such power couple is Donald Trump Jr. & Kimberly Guilfoyle. But how did the eldest child of the former president and the former Fox News host get together in the first place? And what has their romantic journey been like? We’ve got all the juicy details!

November 2007

Back in 2007, Trump and Guilfoyle were more than a decade away from getting together. But they were still friends, having been introduced to each other by mutual acquaintances. But there was no sign of a future romance at the time. Guilfoyle was married to businessman Eric Villency, and had a son, Ronan, born in 2006. Meanwhile, Trump had married Vanessa Trump in 2005. They would stay married for 13 years and have five children together. Their first daughter Kai was born in 2007.

June 2008

In the middle of 2008, we can see Trump and Guilfoyle taking a picture together with their then-spouses. Around this time, the friendship between Trump and Guilfoyle was deepening because his daughter Kai and her son Ronan attended the same private school.

May 2018

Still, when Donald Trump Jr. got divorced, he didn’t waste any time before pursuing Guilgoyle. It was only three months after Vanessa Trump filed for divorce that he and Guilfoyle started dating one another. This caused quite a stir, both because he was the son of the president and because she was a prominent former Fox News host who had left the network to join the Trump-friendly super PAC America First Policies.

The couple ended up making their relationship debut in an unexpected time and place: at Donald Trump’s send-off party for Richard Grenell, the ambassador to Germany.

RELATED: The Unknown Truth About Donald Trump Jr.

June 2018

It’s one thing to debut your relationship at a fancy political shindig, but it’s another to let the world know. That’s why in June 2018, Trump and Guilfoyle made their relationship Instagram official, complete with a picture of the couple posing next to Poison singer Bret Michaels.

June 2018

Much of Trump and Guilfoyle’s relationship seems to be balancing work and pleasure. In June 2018, the two attended the Montana Republican Convention together, and Trump proudly called her his “significant other” during his convention speech. When not playing politics, though, the two found time to go fishing together.

August 2018

You know things are getting serious when a couple creates cutesy nicknames for each other! In August 2018, Page Six reported that Trump likes to call Guilfoyle “Pooh Bear.” But that is downright normal compared to her nickname for him: “Junior Mint”!

September 2018

In September 2018, the two played politics once again by returning to Montana to support Matt Rosendale as he challenged incumbent Democratic Senator Jon Tester during the midterms. Rosendale ultimately ended up losing, but it looks like Trump and Guilfoyle had a good time.

November 2018

This couple doesn’t go much for PDA, but they certainly make plenty of public appearances. In November 2018, they walked arm-in-arm to get a better look at the National Christmas Tree lighting ceremony held at the National Mall in Washington D.C. Donald and Melania Trump helped turn this ceremony into a memorable musical event with performances from veterans of American Idol and The Voice.

RELATED: The Truth About Eric Trump

February 2019

We don’t normally associate Trump and Guilfoyle with being fashion trendsetters. But that didn’t keep them from attending New York Fashion Week in February 2019.

May 2019

By May 2019, Guilfoyle was playing an important role for the Trump family. She now served as a senior adviser for Donald Trump’s re-election campaign, and this meant she and Trump Jr. made a number of appearances together at various Trump rallies.

October 2019

Can you put a price tag on a hug? Maybe! It was cute to see Trump and Guilfoyle hug during their speaking appearance at the University of Florida. Then again, they were paid $50,000 for that brief appearance, so they had a reason for a bit of uncharacteristic PDA.

November 2019

One of the odder events the couple took part in was a joint appearance on The View. The idea was that they would debate the hosts, including Meghan McCain, someone with a real ax to grind. While McCain brought up things like Donald Trump’s attacks on a family whose son was killed while serving in Iraq, fellow host Abby Huntsman tried to deflect a bit by asking when this conservative power couple would be getting married.

July 2020

Considering how much Donald Trump downplayed COVID-19, it was very surreal when he and others in his orbit got it. In July 2020, Guilfoyle tested positive for COVID-19. Trump Jr. tested negative, but both of them canceled their public appearances as a safety measure.

RELATED: The Truth About Barron Trump

August 2020

In the leadup to the 2020 election, things were starting to heat up for Donald Trump. To help get him re-elected, Guilfoyle recorded a fiery pro-Trump speech for the Republican National Convention while a supportive boyfriend waited in the wings.

August 2020

Donald Trump Jr. is an avid hunter, and he helped make Guilfoyle a fan as well. In August 2020, they attended a rally for a new coalition called Sportsmen for Trump, and they kissed during the event.

October 2020

In October 2020, Donald Trump Jr. released a self-published book called Liberal Privilege. And Guilfoyle joined the author for a book signing at the Marriott Hotel in Long Island, New York.

December 2020

With the November election in the rearview mirror, this power couple took things easy ahead of the holidays. They both appeared on a Facebook Live video from his Facebook page to offer thanks for military members and veterans and wish everyone a Merry Christmas.

Meanwhile, Guilfoyle caused a stir with her salsa dance moves the same month at Turning Point USA’s Student Action Summit in West Palm Beach, Florida.


January 2021

After the 2020 election, all eyes were on the Georgia runoff that would determine whether Democrats took control of the Senate. To try to help the local Republicans win, Trump Jr. and Guilfoyle appeared at the Republican National Committee Victory Rally at Dalton Regional Airport in Georgia and even shared a kiss on stage.

RELATED: 7 Outrageous Claims About Donald Trump Made By His Niece

January 2021

The entire Trump clan skipped the inauguration of Joe Biden as president. Instead, Trump Jr. and Guilfoyle took Air Force One down to Palm Beach and began looking for a new place to settle down.

March 2021

March 2021 brought some good news for Trump and Guilfoyle. While they had not yet found the perfect place to live in sunny southern Florida, they did manage to sell their home in the Hamptons (seen above) for a cool $8 million.

April 2021

The search is over! Trump and Guilfoyle bought an 11,300 square foot estate in Jupiter, Florida for $9.7 million. It features a big backyard for their kids to play in and amenities such as a gym and a swimming pool. And if Don Jr. wants to go visit his dad, he’s in luck: Mar-a-Lago is only about a 20-minute drive away!