Red Flags In Tiffany Trump And Michael Boulos' Relationship We Can't Ignore

Donald Trump's daughter, Tiffany Trump, tied the knot with Lebanese American businessman Michael Boulos in 2022 after four years of dating. The couple wasn't in the spotlight much until the 2024 presidential election, when we saw a lot more of them as they came out to support Donald's campaign. Of course, it's easy for folks to wonder about this wealthy, powerful couple that keeps their private life private. So, what's really going on behind closed doors? Are Tiffany and Boulos the perfect happy couple? While we can't be certain, there's one thing about this couple that is for sure: their relationship has a few red flags.
Since Tiffany and Boulos tend to keep things to themselves, it's not as easy to know the ins and outs of their romance as it is with some other celeb power couples. Still, there are aspects of this particular relationship that feel a bit mysterious and somewhat suspect. Will they really go the distance, or are they more interested in appeasing others than making their romance work? While the red flags in Tiffany and Boulos' relationship may not have been obvious at first, these days, they're glaring.

Tiffany Trump is the only child Donald Trump had with the second of his three wives, Marla Maples. After Donald and Maples' difficult divorce in 1999, Maples chose to move to California with Tiffany and raise her away from the public eye. Tiffany told People, "She gave me the chance to have a normal childhood." Clearly, though, Tiffany didn't have her dad around very much growing up. Maples explained, "Her daddy is a good provider with education and such, but as far as time, it was just me." She added, "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."

Now that she is an adult, Tiffany often seems to seek her dad's approval, and rather than avoiding her father's messy world of politics, like her sister Ivanka Trump has learned to do, she makes sure to publicly share her support. She seemingly aimed to be Donald's favorite daughter throughout the 2024 presidential election season. Her apparent desire to win his approval and get more involved in his political career may be evidence that her relationship with Michael Boulos was a calculated choice.

Like Tiffany Trump, Michael Boulos comes from a wealthy family. His family owns the Lebanese vehicle part manufacturing business Boulos Enterprises. Michael's father, Massad Boulos, is a billionaire, and Michael is reportedly the heir to his business and fortune. With the promise of billions of dollars and power in the future, Michael is clearly already wealthier than most people Tiffany could have married. Yet, Michael is worth quite a bit of money before he'll ever get involved in the family business. Per Celebrity Net Worth, Michael is said to already be worth $20 million.

Just because Tiffany and Michael both come from high-profile, wealthy families certainly doesn't mean that the pair was some sort of arranged coupling meant to maximize their wealth and power. After all, it's no surprise that people from these backgrounds would find themselves running in the same circles. Tiffany and Michael met at Lindsay Lohan's club in Mykonos — a hangout spot where you're much more likely to meet fellow wealthy celebs than others. Yet, it's worth noting that before dating Michael, Tiffany had a long-term relationship with Ross Mechanic, who also came from a wealthy family. Mechanic was a registered Democrat, and while there was no indication that this led to the demise of their relationship, it's easy to see how Michael would have been a better pick from a PR perspective.

Money isn't the only thing that may have been at play when Tiffany Trump and Michael Boulos got together. After all, power and politics are equally important to the Trump family. Michael's dad, Massad Boulos, was a big help to Donald Trump as he attempted to secure Arab-American votes during the 2024 election. As a high-profile Lebanese-American businessman, Boulos has many connections and relationships within this community, and he used that pull to help Donald.

While Boulos has always been a Republican, he interestingly didn't get involved in politics until 2019, when he met Donald and their children were already in a relationship. Like his father, Michael, who was born in Lebanon, also assisted in helping Donald win Arab and Muslim American voters' favor. And it's clear that Donald is a big fan of Massad. In October 2024, Donald gave a speech at the Detroit Economic Club while on the campaign trail. He gave Massad, who was in the audience, a shoutout, calling him "a very special man, a great guy," per Fox News. He added, "Many of you know him; he's a very successful man. He happens to be the father of Tiffany's husband, Michael, who's a very exceptional young guy, and she's an exceptional young woman." He then spoiled Tiffany's pregnancy news and accidentally confirmed she's an afterthought compared to Massad, saying, "She's gonna have a baby, so that's nice," before redirecting the attention back to her father-in-law.

Whether or not the joining of the Trump family and the Boulos family was a driving force behind Tiffany Trump and Michael Boulos getting together, it seems that everyone is happy with the result. Tiffany and Michael are included in this since they certainly haven't shied away from leaning into Donald's political ventures. Two of their major relationship milestones even took place at the White House, showing that power and political agenda seem to be on their minds even during some romantic moments.

In 2019, Tiffany made things Instagram official with Michael, hard-launching their romance on Instagram with a photo of the pair in front of the Christmas tree at The White House. In 2021, Michael chose the White House as the setting where he would get down on one knee. He proposed to Tiffany in the Rose Garden with a ring that was said to cost $1.2 million. When Donald Trump left the White House in January 2021, Tiffany posted on Instagram to commemorate the occasion. Alongside a photo of her and Michael at the White House, she wrote, "It has been an honor to celebrate many milestones, historic occasions and create memories with my family here at the White House, none more special than my engagement to my amazing fiancé Michael! Feeling blessed and excited for the next chapter!"

Between their involvement in Donald Trump's 2024 presidential campaign and their unabashed love of the White House, it's clear that Tiffany Trump and Michael Boulos certainly aren't trying to avoid politics. Still, they have kept their relationship private. It's clear that things are headed in a much more public direction for them. Neither Boulos nor Tiffany is very active on social media despite both having many followers. It seems that this is Tiffany's tendency; in an interview with CNN, her former classmate at Georgetown Law School claimed that Tiffany "maintained a very low profile" until graduating in 2020.

If Tiffany and Boulos' relationship really is rooted in a desire to gain power and level up in the political world, then moving further into the spotlight is likely part of their goal. Still, Tiffany and Boulos have had a relatively private life together thus far, and with Donald heading back to the White House and Tiffany and Boulos positioned firmly by his side, they'll likely lead a much more public life than they're used to. And this could shake up any marriage. After all, Donald nonchalantly announced to the world that the couple is expecting their first child, and this surely won't be the last time they'll lose complete control over what the public knows about their personal life.