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

Tiffany Tump and Michael Boulos' relationship looks like a fairytale from the outside. The story of two young members of very rich families who locked eyes during a vacation to Greece and have been inseparable ever since has Hallmark written all over it. In reality though, just like with Tiffany's half-brother Donald Trump Jr. and his ex-fiancé Kimberly Guilfoyle, there are a few relationship warning signs we can't ignore.

One of them? Taylor Swift sang, "I like shiny things, but I'd marry you with paper rings." Though we're not sure Tiffany can relate. She upgraded the engagement ring Michael gave her less than two years after he proposed. As a Daily Mail source claimed in 2022, she'd added larger gems to the tune of $300,000 (taking its total value to $1.5 million). There's nothing wrong with liking fancier things, but changing the look of her ring suggested Tiffany was more interested in its appearance and how much it was worth that its sentimental value. 

The decision may have been deeper rooted too, as Tiffany's dad, Donald Trump, is famous for splashing the cash and putting emphasis on money. The president even joked about the size of his youngest daughter's ring in 2022. While speaking about Toni Holt Kramer, Newsweek reported the president said, "She's worth millions of dollars. She's got a ring on her that's worth $25 million; it's 48 carats." After someone asked about Tiffany's jewelry, Donald hit back, "It is not as big." But this couple may have red flags far deeper than a bling ring.

Though Tiffany Trump and Michael Boulos likely bonded over being members of affluent families, they still grew up very differently. Tiffany was brought up by her mom Marla Maples in California, brushing shoulders with celebrities like the Kardashians. "We were always together, driving me to school, carpooling, singing songs, dancing around, me making fun of her dance moves," she told People in 2016 of her close bond with her mom. "[We knew the Kardashians] like a little a bit. My mom was friends with Kris [Jenner]," she added. But, despite being cozy with the reality stars, Tiffany was largely shielded from her dad Donald Trump's celebrity and didn't live life in the gossip columns. "[My mom] moved us out of New York to get out of the spotlight and let me grow up and find my own identity versus being in the shadow of a name or growing up very young with all that pressure. So, she wanted me to have a chance to have a normal childhood," Tiffany added.

Michael's upbringing was vastly different, though. He was born in Texas but grew up thousands of miles away from the glitzy allure of Hollywood in Nigeria. Michael also didn't seem to be so shielded from his family's notoriety. The Boulos gang is made up of well-known business people and his brother is the rapper Farastafari.

It's certainly no red flag for people from different continents and backgrounds to fall in love, but Tiffany and Michael could experience a culture shock. While many couples bond over shared experiences, such as watching the same TV shows or listening to the same music during childhood, the duo may find they don't have the same pop culture references.

Having family members in high places could be something Tiffany Trump and Michael Boulos bonded over, but it could also be detrimental to their relationship. In 2024, AP claimed Donald Trump and his team were hoping Massad Boulos could help him secure votes from the Arab-American community for his re-election bid. As Susan Trombetti, matchmaker and CEO of Exclusive Matchmaking, explained to Glam, that could be a bad sign. "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 shared.

But things took another high-pressure turn after Donald won the election and appointed Massad as his senior Middle East adviser. "Obviously the No. 1 point that is of high priority within the Arab-American community is the current war in the Middle East. And the question is, who can bring peace and who is bringing war? And they know the answer to that," Massad said. While it's a green flag when the families of a couple get along, that can turn red when work is involved. Donald and Massad being so closely linked in such high-profile and stressful roles has the potential to put a serious strain on their relationship and their children's. If tensions between Donald (who's not exactly famous for being calm and collected) and Massad flair, it could trickle down and cause disagreements between Tiffany and Michael.

Though the four years between Tiffany Trump and Michael Boulos' is nothing compared to some of the celebrity couples who rightfully forced us to confront our fixation with age-gap relationships, it could still cause an issue. Dating coach Jake Maddock claimed cis women in relationships with younger, cis men can sometimes find their maturity levels don't match up. "Men and women mature emotionally at different times. According to experts, men take about 10 years longer to become emotionally mature than for a woman," Maddock told Daily Mail. He suggested the ideal age ratio in straight relationships is a woman being five to 10 years younger than her male partner (though science has claimed a three-year age gap is ideal for a successful relationship). 

The dating coach also told the outlet a few extra years between men and women can help with some fundamental foundations of a healthy relationship. "He will also have a more mature viewpoint when it comes to solving problems and relationship issues," Maddock said.

Marrying into one of the richest, most high-profile families in the world is no easy feat for anyone, but add in a father-in-law who announces your personal news to the world before you can? Red flag. That's what happened to Michael Boulos, as Donald Trump very publicly confirmed Michael and Tiffany Trump were expecting their first child together before they made their announcement.

Donald was speaking about Massad Boulos at the Detroit Economic Club in October 2024 when he let the baby bombshell slip. Referring to Massad, who was in the audience, Donald said, "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. And she's going to have a baby. So that's nice," (via People). Donald's announcement appeared to be a throwaway remark, suggesting it wasn't planned. And it's unclear whether he had the couple's permission.

If he didn't, that's a problem. A 2014 study of 52 divorced couples found a lack of support from family members was one of the leading causes of marriages ending. And the businessman sharing such big, personal news with the world without Tiffany or Michael even being there wasn't exactly supporting his daughter and son-in-law.