When Did Donald Trump Jr. And Kimberly Guilfoyle Get Engaged?

Donald Trump Jr. found love again after splitting from ex-wife Vanessa in March 2018. That same year Don Jr. began dating Fox News host Kimberly Guilfoyle, with their relationship being confirmed barely three months later in June. Since then, the pair have remained close, even taking their relationship to the next level by getting engaged. Although it appears they wanted to keep that tidbit under wraps.

Trump Jr. reportedly popped the question on New Year's Eve in 2020. It's unclear where or how he proposed, but the couple's big news was not made public until January 4, 2022, when an insider told People that Guilfoyle had been sporting an engagement ring for a while. The ring in question may have been featured days prior in Guilfoyle's January 1, 2022 Instagram post where she posed alongside Trump Jr. in several photos while wishing him a happy birthday. As of today, the two have not publicly announced their wedding plans, but it appears they have been living life as a married couple, or the closest thing to it.

Neither Donald Trump Jr. nor Kimberly Guilfoyle have confirmed their engagement date. Still, that hasn't stopped the children's book author from wishing her beau a happy anniversary on Instagram in both April and May 2024. It's unclear what milestones Guilfoyle is celebrating, but the dates appear to align with the start of their relationship.

On April 24, 2024, Guilfoyle shared a post where she's all smiles next to Trump Jr. In the caption she penned a sweet message: "Happy anniversary to my sweetheart @DonaldJTrumpJr. You are my best friend and my soulmate. Here's to us and our incredibly blessed life we share together. Looking forward to creating new memories and enjoying more adventures together." A week later, Guilfoyle shared a similar message on May 1, 2024, where she seemingly marked the occasion again. Or did she? Over on Trump Jr.'s page, he also celebrated their anniversary on April 24, 2024 with a message of his own that acknowledged six years with the media personality. Unlike Guilfoyle, he did not post a follow-up on May 1, which raises questions about her second anniversary message.

Before Donald Trump Jr.'s divorce was finalized with Vanessa Trump, she spoke up in support of Kimberly Guilfoyle. She slammed an article published by the NY Daily News, which called for Guilfoyle to be fired from Fox News for dating President Donald Trump's son. Vanessa didn't agree that Guilfoyle should lose her career simply due to her relationship. "The lengths people will go to attack a woman simply because she's dating Don. We've been separated for over 9 months and respect each other's decisions & privacy. We'll focus on raising our great kids. Would be nice if the press did the same rather than obsess over our pvt lives," her tweet read.

It appears the children Vanessa shares with Trump Jr. also approve of Guilfoyle. In April 2023, Guilfoyle shared a photo for Easter that included Don Jr.'s five children: Kai Madison, Donald III, Tristan, Spencer, and Chloe. Kimberly Guilfoyle's son Ronan Villency was also included in the image, which shows that the couple has been able to blend their families since becoming engaged. The two may not have walked down the aisle as of today, but Trump Jr. and Guilfoyle's engagement is still going strong.