Our Matchmaker Reveals The Red Flags In Tiffany Trump's Marriage

The Trump family doesn't exactly have a reputation for lifelong marriages, and while we hope that Tiffany Trump and her husband Michael Buolos can make it last, it's also become clear that there are some glaring red flags in their relationship. After meeting at Lindsay Lohan's club in Mykonos back in 2018, the couple hosted a Mar-a-Lago wedding in November 2022, and in October 2024, her father, Donald Trump, announced at a campaign event that Tiffany is expecting her first child. Tiffany is the only child of Donald Trump and his ex-wife Marla Maples, and the second youngest of Donald's five kids. Meanwhile, Buolos is the Lebanese son of a businessman who grew up in Nigeria. As the children of fabulously wealthy and successful parents, the pair appear well-matched on paper. However, there's more to a good marriage than family pedigree.

To suss out the couple's future, our sister site Glam got the exclusive word from Susan Trombetti, matchmaker and CEO of Exclusive Matchmaking, on why she thinks their marriage might not work out. She does admit that Trump and Boulos have a basic level of compatibility on the surface, of course. "Both are from billionaire families and there is an expectation that you marry someone appropriate who can keep up the image instead of whoever you might want to love," she explained. However, she points out that their relationship might be based on material wealth, and may not have lasted if they didn't have similar financial backgrounds. Nevertheless, all that family money will help Buolos keep up with Tiffany Trump's lavish lifestyle. Trombetti added, "We have seen it in movies. It's the one that makes a good match for the family instead of the one that might make you feel crazy with passion. This could be similar to an arranged marriage."

As they say, when you marry someone, you're not just marrying them, you're marrying into their family — and the Trumps are quite the family to marry into. Susan Trombetti pointed out that Michael Buolos might have a hard time adjusting to the 24-hour media spotlight that exists around the Trump family name, saying, "They are always under the microscope with [Donald] in the front and center." But it's not just Donald Boulos has to contend with. With the Trump family name comes all of the people who want to find political favor with the president, and by extension his family. "It can't be easy to constantly be on the lookout while trying to remain private. It must cause pressure and stress within the marriage," Trombetti acknowledged.

While Tiffany has been present at her father's political rallies, it's well known that Ivanka, Don Jr., and Eric get more of the spotlight. Even Barron Trump is becoming one of the most talked-about members of the family. That leaves Tiffany as the odd woman out of the Trump inner circle, which could cause some marital awkwardness, according to Trombetti. "Tiffany and Michael Boulos, by extension, seem like the stepchildren on the outside looking in, always craving acceptance from the family. She isn't the child of Ivana Trump and those siblings all seem to be very bonded; she appears as if she is on the outside," she explained. 

Meanwhile, Buolos' Instagram makes it look like he's quite close with his family, which could only exacerbate Tiffany's lesser position. "If you are a person that thinks family is important, this is a hard pill to swallow knowing she is the afterthought child, although I am sure Donald loves her as much as the others," Trombetti added. 

There's also the pressure of being related to someone who called the country where Michael Buolos grew up a "s***hole" country. And while Donald Trump's remarks apparently didn't faze his daughter, with a source telling People, "Tiffany's not keeping her finger on the pulse of that BS," a Nigerian ambassador to the U.S. called the remarks "deeply hurtful, offensive and unacceptable" (via Reuters). To complicate talking politics further, Trump (sort of) walked back his harsh statement on the country, denying he said it and instead reframing his words on X, formerly known as Twitter, as "tough" language. Tiffany and Michael probably wished they could brush the whole thing under the rug, but then, per the AP, Donald enlisted Michael's father, Massad Buolos, to try and persuade the Arab community to vote for him in the 2024 election. 

It's a head-spinning amount of extra-marital responsibility for Tiffany and Michael to keep track of their parents' motives, with Susan Trombetti pointing out, "Boulos' connections to the Arab world are being leveraged and possibly exploited through Michael's father-in-law. I feel like that could be a lot of pressure." In the end, there are enough red flags to make anyone nervous about the future. And with Donald returning to the White House in 2025, the scrutiny is only going to increase on everyone in his orbit, including Tiffany and Michael. Trombetti summed it up by saying, "People either love or hate Trump, and he is so polarizing, so this must be a tough one being in the family when you have these extremes of people's politics out there." On the plus side, Tiffany's husband's connections might finally provide Melania with a way to send those mirrors to Africa.