Kimberly Guilfoyle & Don Jr.'s Age Gap Is Bigger Than You Might've Known

Kimberly Guilfoyle made a desperate move to prove that Donald Trump Jr. hasn't replaced her with a much younger woman. After the Daily Mail published a report claiming that Donald Jr. had been spied kissing a dinner companion, 37-year-old socialite Bettina Anderson, Guilfoyle posted a series of photos on Instagram. In one of them, she's staking her claim on her man by giving him a smooch.

According to The Washington Post, Guilfoyle and Trump met sometime around 2006 — the year Guilfoyle and California Governor Gavin Newsom divorced. A friendship blossomed between the pair because they had children who attended school together, providing ample opportunity for them to bump into each other. While they have kids who are nearly the same age, the couple has a large age gap — Donald Jr. is nine years younger than his fiancee, who celebrated her 55th birthday in March 2024. This was five months before Donald Jr. was seen locking lips with Anderson. Donald Jr.'s stepmother, Melania Trump, is one year younger than Guilfoyle.

It wasn't until over a decade after they met that Guilfoyle and Donald Jr. started dating. One major obstacle in the pair getting together was Donald Jr.'s marriage to Vanessa Trump. Just two months after Vanessa's 2018 divorce filing, Page Six reported that Guilfoyle and Donald Jr. were seeing each other. They got engaged in 2020, and Guilfoyle has compared her assimilation into the Trump family to "The Brady Bunch." However, her relationship with Donald Jr. is too spicy for '70s primetime television.

Kimberly Guilfoyle seems pretty proud of her relationship with Donald Trump Jr. Per The Washington Post, the former Fox News personality was addressing a group of teens in 2018 when she said of her then-nascent romance, "I mean what can I tell you? Mama's a closer, you know what I mean?" Guilfoyle has reportedly made other awkward comments about her relationship. In his book "Frankly, We Did Win This Election," author Michael C. Bender claims that Guilfoyle told Republican donors that Donald Jr. likes her to dress up as a cheerleader. She also reportedly described her fiancé as "naughty."

It's not just role-playing that Guilfoyle uses to keep the flame burning hot but the reinforcement of outdated gender roles. "I love taking care of Don, the way that I saw my mother lovingly take care of my father," she told Metropolitan Luxury Magazine in 2022. "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." When she cooks for her man, she also does it in style. Guilfoyle has shared videos of her unusual kitchen attire, which consists of impractical garb such as tight dresses and sky-high platform sandals. Donald Jr. has also taken Guilfoyle fishing, but there's no word on whether she fried up their catches while wearing a cheerleader costume.