Red Flags In Tiffany Trump's Marriage, According To Our Matchmaker

Of all the Trumps, it's obvious that Tiffany Trump is the one who likes to keep a low profile, but that doesn't mean that her life isn't under scrutiny. The youngest daughter of Donald Trump has made headlines a few times in the past, including the times she was spotted wearing inappropriate outfits, or when she showed off her natural makeup-free beauty at college. Tiffany also caused a stir when she hard-launched her relationship with Michael Boulos on Instagram in January 2019. Naturally, many were curious to learn more about him and it turns out that he comes from a well-established family as well that runs a very successful distribution and trading business, with a focus on motorcycles and power bikes, based in Nigeria, where he grew up.

Tiffany and Michael married in 2022, and although their relationship seems pretty drama-free, it doesn't come without some hurdles. Susan Trombetti, matchmaker and CEO of Exclusive Matchmaking, told Glam exclusively that she sees issues that can stem from their high-profile families, rather than between the couple. Although Tiffany and Michael are expecting their first child together, the cards are still stacked against their marriage with several red flags that are waving loud and clear.

Tiffany Trump and Michael Boulos both come from money — and lots of it. While that may seem like a match made in heaven, Susan Trombetti thinks that comes with added pressure from both sides. "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," the matchmaker exclusively told us.

While Trump and Boulos reportedly met at Lindsay Lohan's Mykonos club in 2018, it's no surprise that they gravitated toward each other. They may have initially started dating based on their mutual romantic or sexual attraction, but who knows if their relationship would have lasted if either one wasn't wealthy. Trombetti pointed out, "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."

It's no secret that the word on the street is that Donald Trump's favorite offspring is Ivanka Trump. Before the former model stepped away from politics, she was by her father's side during his campaign and was hired by him as his senior advisor in the White House. Additionally, Donald's two older sons, Eric and Donald Trump Jr., have been active in his political ambitions as well, while Tiffany Trump has made fewer appearances. Matchmaker Susan Trombetti noted exclusively to Glam, "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."

Michael seems to be very close with his family and often shares pics of them on his Instagram feed. Trombetti pointed out, "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." It remains to be seen, however, as Donald has publicly snubbed Tiffany several times. In one instance during the 2024 Republican National Convention, captured by The Recount on X, formerly Twitter, Tiffany was seen trying to give her father a kiss on the cheek, only to have him ignore her. Ouch!

Before Tiffany Trump met Michael Boulos, whose family is Lebanese but hails from Nigeria, Donald Trump referred to African nations using an offensive slur, per NBC News. The "Apprentice" star later backtracked with his X post: "The language used by me at the DACA meeting was tough, but this was not the language used." Despite his diss, the 2024 presidential hopeful is still trying to use Michael's family to get votes. As reported by AP, Donald enlisted Michael's father Massad Boulos to convince the Arabian community to vote for him.

We know that family and politics don't mix well and relationship expert Susan Trombetti thinks that's one big red flag. " ... 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," she stated in our exclusive conversation. Additionally, Tiffany and Michael are expecting their first baby together, but with the upcoming election, it's all about The Don. "Forget what they might want to do; their life revolves around Donald for now," Trombetti quipped.

As Donald Trump and Marla Maples' daughter, Tiffany Trump has been well-known for most of her life, but Michael Boulos grew up relatively outside of the spotlight. That all changed when the two became linked and are now thrust even more in the public eye because of Donald's name constantly in the headlines, which Susan Trombetti exclusively pointed out to us. "They are always under the microscope with Trump in the front and center," she stated.

What's more, Tiffany and Michael have to be wary of others possibly using them for the Trump name. "Many people are trying to gain favor on top of that because he is the former president and the current Republican nominee. 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 declared. If Donald does indeed become POTUS for the second time, that'll add even more strain on Tiffany and Michael to maintain a perfect image, and any hint of marital problems is bound to be made public.  

It's safe to say that Donald Trump is one of the most controversial political figures in history. From being a convicted felon who's running for the presidency to slamming immigrants, it's no wonder that many give him a thumbs down. Unfortunately, the public's ire can also trickle down to Tiffany Trump and her husband Michael Boulos. "All of the folks who are against Trump probably take it out on them by association and perhaps they are shunned in certain circles," Susan Trombetti speculated.

There's a reason Tiffany keeps her inner circle super tight, and by now, her friends likely keep their opinions about Donald to themselves. However, Michael and his family are dealing with backlash from the Arab community after his father Massad Boulos aligned himself politically with Donald. As AP reported, many Arab-Americans claimed that Donald showed more support for Israel than President Joe Biden and has made anti-Islamic comments in the past. Throw Michael's Lebanese heritage into the mix, and being Donald's son-in-law has got to be hard on him. Trombetti exclusively told Glam, "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." Perhaps Tiffany should go by the last name Boulous instead.