Kimberly Guilfoyle & Tiffany Trump Are Closer Than We Thought

There are a lot of conflicting reports regarding how Donald Trump Jr.'s siblings feel about Kimberly Guilfoyle. Some sources suggest that the former Fox News host appears to have ingratiated herself with the Trumps, while others claim that Ivanka Trump's relationship with Guilfoyle might be rocky and hostile. There are also rumors that Donald Trump isn't a fan of Guilfoyle and is beginning to tire of her. However, Tiffany Trump is a big fan — and her friendship with Guilfoyle is closer than most would imagine.

Guilfoyle was keen to show her adoration for her future sister-in-law on Instagram in October 2021 for her birthday. She posted a series of pictures, including images featuring herself, Donald Trump Jr., Lara Trump, Tiffany, and her husband Michael Boulous. "Happy birthday to my angel @tiffanytrump! I love you to pieces!" Guilfoyle gushed. She was back spreading the social media adoration again in November 2023. "Happy anniversary, my love! So grateful to walk through life with you!" Tiffany captioned a carousel of photos from her wedding day. Guilfoyle was totally there for it. "Happy anniversary, sweethearts; we love you!" she wrote in the comments.

In a display of affection and, perhaps, political maneuvering, Guilfoyle took to social media again in March 2024. Posing with prominent figures from the MAGA movement, including the controversial pardoned felon Roger Stone, Lara, and Tiffany, Guilfoyle's message was clear: "The best is yet to come," she vowed ominously.

It makes sense that Tiffany Trump would befriend Kimberly Guilfoyle. Donald Trump's youngest daughter has always been the forgotten one, having little to do with her father growing up. "Her daddy is a good provider with education and such, but as far as time, it was just me," Tiffany's mom, Marla Maples, told People in April 2018. "Her father wasn't able to be there with day-to-day skills as a parent. He loves his kids. There's no doubt. But everything was a bit of a negotiation."

Tiffany knows what it takes to gain entrance into the Trump inner sanctum. So, she's in a prime position to give Guilfoyle some much-needed guidance. Meanwhile, Guilfoyle is likely grateful for any help she can get, especially given she was (wrongly) accused by some of being the reason Donald Trump Jr.'s wife, Vanessa Trump, divorced him.

Tiffany welcomed Guilfoyle into the family with open arms. She ensured she was front and center at her November 2022 wedding to Michael Boulous at Mar-a-Lago, which, in true Trump style, involved an inevitable tsunami of drama. Guilfoyle displayed her unique style by dressing in all black for the celebration. At the same time, other guests chose more traditional and fitting pastel colors. It's safe to say the decision did not go down well. In fact, Ivanka Trump even unceremoniously chopped Guilfoyle out of one of the wedding pics — sparking yet more rumors of an ongoing feud between the two.

Kimberly Guilfoyle and Tiffany Trump were united in fashion for the 2019 State of the Union address. They wore all white, in stark contrast to their fellow Republicans, such as Melania Trump, who was decked out in one of her usual Stasi-style outfits — this time, a black $2,390 Burberry military coat dress paired with black leather gloves.

Female Democrats had announced they would be dressing in all white to stand in solidarity with women and unite against Donald Trump. Florida Rep. Lois Frankel expressed this sentiment, posting on X, formerly known as Twitter, "By wearing suffragette white to #SOTU2019 tmrw we're sending a message to everyone that voted for @HouseDemocrats & delivered us the majority that we're working #ForThePeople, promoting the economic security of women & their families!"

Tiffany kept quiet regarding the clothing decision, but Guilfoyle was characteristically vocal and combative. "Memo to Democrats: You don't own the votes of all women, and you don't own wearing the color white! @realDonaldTrump is fighting every day to advance the interests of women across the country, and I'm proud to stand with him. #WGDP," she tweeted. Many begged to differ about Donald's commitment to women's rights. "Get a clue. They are trying to dismantle a constitutionally protected medical procedure. They want to control women's personal lives and take our freedom of choice away. No woman with intelligence listens to those like you. Trumplicans are anti-woman. They hate us," one critic wrote.