How Long Have Donald Trump Jr. And Kimberly Guilfoyle Been Engaged?

Donald Trump Jr. and Kimberly Guilfoyle have been called the "prom king and queen of MAGA land" by Business Insider, but even high school royalty has to graduate eventually, leaving many to wonder when the conservative couple will get hitched. Trump Jr. and Guilfoyle's relationship timeline stretches back to their Instagram launch in June 2018. They shared their engagement on the same platform — two years after the fact. 

Guilfoyle posted an Instagram photo on New Year's Day 2022 of her and Trump Jr. posing in front of a Christmas tree. For the most part, the picture looks like any other the couple has posted over the years — until you spot the giant diamond ring on Guilfoyle's left ring finger. "I can't wait to spend the rest of our lives together," Guilfoyle wrote.

This was widely seen as the couple's official engagement announcement. However, two days after Guilfoyle posted her holiday pic, inside sources told the Daily Mail: "Don and Kim got engaged on New Year's Eve 2020 – which is Don's birthday. They've been together for almost four years now and have been friends for 15 years.'

Donald Trump Jr. and Kimberly Guilfoyle kept their engagement under wraps (from the press)

According to the Daily Mail's sources, the eldest son of former President Donald Trump and the former Fox News personality chose to keep their engagement from the press as they settled into their new Floridian digs. Sources said the couple wanted to focus on their work and their large family. Donald Trump Jr. has five children with his ex-wife, Vanessa Trump, and his bride-to-be has one son with Eric Villency, from whom Guilfoyle had her second divorce in 2009.

Still, that doesn't mean the happy couple kept their engagement a secret from everyone. "It's been an open secret for the past 12 months," a Daily Mail source revealed, "with everyone Kim runs into admiring her almost 8-carat diamond engagement ring. The chatter about the engagement has increased since the engagement ring was seen on Don and Kim's Instagram accounts on New Year's Eve."

Guilfoyle was more blatant about their relationship upgrade in a Valentine's Day 2022 Instagram post. "Falling in love with my fiancé more and more every day," Guilfoyle wrote. "You're my best friend, my support system, and my forever guy." Based on the Daily Mail's inside sources, Guilfoyle and Trump Jr. would have been engaged for two years and two months at the time of her post.

The conservative couple has been equally tight-lipped about future wedding plans

Considering Kimberly Guilfoyle and Donald Trump Jr. waited two whole years to announce their engagement to the rest of the world, it's unsurprising that they would be just as conservative with the news they share regarding their future nuptials. At the time of this writing, no date has been set. During a September 2023 interview with Greg Kelly of Newsmax, the television personality made it clear she had no plans of divulging that information anytime soon.

When asked if a date had been set for her wedding, Guilfoyle curtly responded, "Uh, not that I'm sharing on the air" (via The Independent). However, she did confirm her long-time engagement to Trump Jr., prompted by Kelly referring to former President Donald Trump as Guilfoyle's "potential" father-in-law. "Potential? Future father-in-law. Jesus," Guilfoyle said. After Kelly revealed he didn't know she was engaged, she replied, "We've been engaged, babe, for two years, but we'll take this breaking news alert. That's hysterical."

Following Tiffany Trump's stunning wedding in 2022, Guilfoyle and Trump Jr. are the only couple in the Trump family yet to wed. Given the couple's previous track record, one could reasonably bet we might find out about their wedding years after the fact in a social media post.