Kimberly Guilfoyle & Don Jr. Have A Bigger Age Gap Than We Knew

There's a surprisingly large age gap between Kimberly Guilfoyle and Donald Trump Jr. The couple started dating in 2018 following Don Jr.'s messy divorce from his ex-wife Vanessa Trump, with whom he shares five children (Guilfoyle was also previously married, to California Governor Gavin Newsom and Eric Villency, with whom she had one son). After two years of dating, Guilfoyle and Don Jr. became engaged in late 2020 but didn't confirm the news until January 2022. Sources revealed to the Daily Mail that Don Jr. proposed to Guilfoyle on his birthday, December 31. "It's been an open secret for the past 12 months," an insider confirmed at the time. "They've been together for almost four years now and have been friends for 15 years." And, as it happens, the former Fox News host is significantly older than her husband-to-be. 

Guilfoyle turned 55 in March 2024, while Don Jr. celebrated his 46th birthday in December 2023, leaving a roughly nine-year age gap between the couple. Despite this noticeable difference, Guilfoyle proudly shared what makes them such  a great team during a 2022 interview with Metropolitan Palm Beach. "We are similar in many ways and beautifully complement one another in other ways, a true yin and yang. We share the same inner passion and fighting spirit," she gushed. 

The staunch Trump loyalist and outspoken political commentator added that her core values also play a major role in keeping their relationship both strong and fair. "I love being an independent career woman and strong female, with my own opinions and passions. Don loves that I am traditional and yet fiercely independent," she explained. "We are partners in this incredible journey they call life, and I totally love it!"

It's worth noting that Kimberly Guilfoyle and Donald Trump Jr.'s surprisingly large age gap is a mere drop in the bucket compared to the significant age difference between his father, Donald Trump, and wife Melania Trump. The former president first met Melania at a New York Fashion Week party in 1998 when he was 52 and she was 28, which means that the Trumps have a whopping 24-year gap between them. In fact, this puts the former model much closer in age to her son-in-law Don Jr., with only eight years between them, as well as to her daughter-in-law, Ivanka Trump, with their difference being just 12. But, in a May 2005 interview with Larry King, which was broadcast on CNN, the former first lady described her connection with Donald as instantaneous.

"It was a great chemistry and energy. We had a great time, we start to talk. You know, something was there right away," Melania recalled. For his part, Donald enthused about their relationship dynamic: "We literally have never had an argument or — forget about the word fight. We never even had an argument." He stressed, "We're just very compatible. We get along. We just have a very good relationship." However, recent developments suggest that Donald and Melania's marriage might be on the rocks, with whispers of an impending divorce. Similarly, Guilfoyle and Don Jr. are also facing rumors of relationship trouble especially after Don. Jr was seen publicly kissing model Bettina Anderson in August 2024, according to eyewitnesses who spoke to the Daily Mail.