While Donald Trump is still in the news, his son Donald Trump Jr.'s relationship with his fiance Kimberly Guilfoyle is in the spotlight just as much. Although Trump has been married three times, Donald Jr. was married to Vanessa Kay Haydon from 2005 to 2018, and he plans to marry Kimberly Guilfoyle. It will be the third marriage for Guilfoyle, who was previously married to Eric Villency and Gavin Newsom, who is the Governor of California.

Donald Trump Jr. and Kimberly Guilfoyle are both very active on Instagram and often post about their romance, sharing how they feel about each other. They also share quite a lot about the time that they spend with his children, which allows their followers to see what their lives are really like.

Donald Trump Jr. And Kimberly Guilfoyle Have A Close Relationship

Donald Trump Jr. went to the Playboy mansion when his ex-wife Vanessa was pregnant with one of their five children, but although the couple was married for over a decade, he has moved on. Judging from what he posts on his Instagram account and the way that Kimberly Guilfoyle gushes about him, they have a happy relationship.

According to People, Trump Jr. and Guilfoyle started seeing each other in 2018 and got engaged in January 2022. While he lived in New York City before, they purchased a mansion in Jupiter, Florida. The New York Post reported Jared Kushner and Ivana Trump were also living in Florida at that time.

Donald Trump Jr. and Kimberly Guilfoyle smiling at Christmas
An image of Donald Trump Jr. and Kimberly Guilfoyle smiling in front of a Christmas tree
via Instagram

According to The New York Post, they bought a house that cost $9.7 million. It has a pool, a huge outdoor area, a fancy kitchen, a gym, and high windows.

Guilfoyle was on the cover of Metropolitan Magazine in December 2022 and shared more about her relationship with Donald Trump Jr. She said that he likes that she is "traditional and yet fiercely independent" and called them "partners in this incredible journey they call life."

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She also shared that she likes cooking and other domestic pursuits. She told the magazine, "I love taking care of Don, the way I saw my mother lovingly take care of my father. 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 celebrated her 54th birthday on March 9th, 2023, with a party at their Florida house. According to SF Gate, around 400 guests were there, including Trump, who danced.

Trump Jr. shared a birthday message on Instagram for his partner. He wrote, "Happy birthday to the best broad ever @kimberlyguilfoyle (inside joke but she knows that’s the highest form of compliment ever!)" He added, "29 only comes once or twice so enjoy it princess. I love you."

Donald Trump Jr. and Kimberly Guilfoyle posing for photo at an event
Donald Trump Jr. and Kimberly Guilfoyle standing together at an event in front of tables and flowers
via Instagram

While Trump Jr. is of course part of a very public family, he and his fiance seem to enjoy regular date nights and a lot of time together. He posted a video of Guilfoyle playing golf and praised her for doing so well with the sport. The two are also heavily involved in charities and often attend fancy events. She often calls him "my honey" in her posts and seems to enjoy cooking for him and his kids, as she shared once in 2020 that she made fish tacos for dinner.

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Guilfoyle often shares messages for the couple's April anniversary about how much she loves Trump Jr. In 2020, she wrote about the romantic gestures that he had made: "we were able to take some time to celebrate two amazing years of being together. It has been a very special time and he was so thoughtful with his card, balloons, chocolate covered strawberries (one of my favorites), and beautiful flowers. I kept up my cooking with KG and we enjoyed a great meal. We truly are blessed and I love having him as a wonderful other half."

For their 2021 anniversary, she wrote, "Happy Anniversary to my love! The past 3 years have been amazing, filled with adventure and memories that will last a lifetime! Here’s to many, many more @donaldjtrumpjr I love you!"

The Truth About Donald Trump Jr. And Kimberly Guilfoyle's Family

Kimberly Guilfoyle seems very comfortable around Donald Trump Jr.'s five children. He and Vanessa are parents to 8-year-old Chloe Sophia, 11-year-old Tristan Milos, 10-year-old Spencer Frederick, 14-year-old Donald III, and 15-year-old Kai Madison. Guilfoyle also has a 16-year-old son named Ronan from her marriage to Villency.

The couple often posts about the great times that the family has together. In 2016, Donald Trump Jr. posted a photo to his Instagram account of him and his youngest daughter taking a nap. He wrote in the caption, "Nap time with Chloe Sophia. Doesn't get better than that. #familytime."

Donald Trump Jr. and daughter Chloe smiling and standing together
Donald Trump Jr. posing for a photo and smiling with his daughter Chloe
Via Instagram

The pair spent the 2023 spring break together and Trump Jr. posted several photos of the family fishing and enjoying some time on a boat. He often refers to the kids as "the Smurfs" and did so this time, too. He wrote in the caption, "Great time with the @kimberlyguilfoyle and the Smurfs for their spring break!!! Now I need a vacation from dealing with the monsters."

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Guilfoyle seems to love spending time with her fiance's children, and she shared a snapshot of a regular family weekend that involved playing basketball and getting some treats at Southern Belle's Cakery, a bakery in Palm Beach, Florida.

The couple's personal life seems all about family hang-outs and holidays. There are countless posts on both of their Instagram accounts about celebrating Thanksgiving and Christmas, and Trump Jr. seems to spend a lot of time with his children. In January 2023, he took his five children to an amusement park and wrote "Great day with the Smurfs."

Donald Trump Jr. and Kimberly Guilfoyle smiling in a selfie
An image of Donald Trump Jr. and Kimberly Guilfoyle standing outside and smiling
via Instagram

In 2022, Donald Trump's daughter Tiffany Trump married Michael Boulos, and according to People, the wedding took place at Mar-a-lago. Trump Jr. Guilfoyle, and Trump Jr.'s children were there, too, and he shared some photos of the kids in their formalwear. He wrote in the caption, "​​​​Great time with the Smurfs at Tiffany’s wedding yesterday. The little one were all in it and were perfect… not that there was ever any doubt."