Red Flags In The Trump Family Relationships We Can't Ignore

When the Trumps aren't engaged in messy feuds, they're entangled in their arguably messier love lives. Over the years, there have been an awful lot of weddings, divorces, and prenups within the Trump dynasty. Family patriarch Donald Trump has been married three times. Donald and his first wife, the late Ivana Trump, encapsulated the yuppie aesthetic of the '80s, all big hair and lavish living. However, their relationship also bore some glaring red flags. Donald cheated on Ivana with Marla Maples, who would go on to become his second wife. 

But Donald and Maples' marriage was also a red flag-fest, with the mogul seemingly feeling rather disappointed when his second wife announced that she was pregnant with Tiffany Trump. Thereafter, he wed the much younger Melania Trump, a marriage that has proved far from a fairytale (even the typically stoic Queen Elizabeth II reportedly had her suspicions about Donald and Melania's marriage).

And Donald's children, it seems, have inherited this tendency toward messy relationships, experiencing breakups, makeups, and ugly divorces. In fact, even the most seemingly "normal" or the Trump kids haven't been immune from problematic relationships. The Trump family is no stranger to a troubled marriage or two (or three ... ). Let's take a deep dive into red flags in the Trump family relationships we can't ignore.

The erstwhile Melania Knauss set forth to the U.S. in the mid '90s in pursuit of modeling work. In 1998, she met Donald Trump at a nightclub and he attempted to charm her. But there were red flags from the outset. Donald had a date with him when he asked for Melania's number, which led to her initially rejecting his advances. Soon enough, however, she agreed to a date and the pair went on to wed in a lavish ceremony in 2005.

Their relationship only got stranger as the years went on. In fact, they hardly spend any time together and sleep in separate beds. "I don't know any couple that spends as much time apart," Melania's biographer Mary Jordan told The Guardian. "They are often in the same building, but nowhere near each other. She rarely goes into the West Wing. She doesn't like to golf ... She likes to be isolated. She is a loner. He is a loner."

This might lead some folks to wonder why the Trumps bother staying married (Donald himself told Fox News that Melania's concern following his 2024 assassination attempt means that she likes him, or possibly loves him). According to Melania's friend Stephanie Winston Wolkoff, the couple has a transactional relationship, which is arguably a red flag in itself. "I do believe it is a transactional marriage," Wolkoff told the BBC. "I mean, Donald, you know, Donald got arm candy ... And Melania got two dynamic decades." 

Melania and Donald Trump's marriage is one built on antiquated gender roles. When Melania announced that she was pregnant with the couple's first child — and Donald's fifth — in 2005, her husband was surprised rather than overjoyed. Preparing for the baby was left entirely up to Melania, who would wake up at 7 a.m. to create a nursery space for her little one. "We know our roles," Melania told Parenting.com (via GQ). "I didn't want him to change the diapers or put Barron to bed."

Donald himself has stated that he believes changing diapers is emasculating. "There's a lot of women out there that demand that the husband act like the wife, and you know, there's a lot of husbands that listen to that," he said during an appearance on "Opie and Anthony" (via BuzzFeed) in 2005. "So you know, they go for it." In fact Donald declared that, had he married a less maternally-inclined woman, he probably wouldn't have had Barron in the first place. 

It wasn't just changing diapers that was off the cards for Donald. In 2006, a pregnant Melania told People that her husband likely wouldn't be taking the baby on any outings either. "I don't expect him to walk down Fifth Avenue with a stroller," she said. But unequal division of labor can put a strain on marriages, with some women resenting their husbands as their domestic duties mount.

Ivanka Trump and Jared Kushner's marriage may appear solid on the outside, but scratch the surface and there are red flags aplenty. There once was a time when "Javanka" almost didn't come to be. In his book "Breaking History: A White House Memoir," Kushner revealed that in 2007 he broke up with Ivanka after months of dating. He wanted to marry a Jewish woman, a sentiment shared by his mother, who disapproved of Ivanka and urged Kushner to call it quits. "When I realized that I was falling in love with Ivanka, I grew concerned about our different religions," he wrote. "As hard and painful as it was, I broke up with her."

A few months later, the couple was reunited at a party and Ivanka told her ex that she would consider converting to Judaism for him. Accordingly, they rekindled their romance and Trump began the conversion process. It seems that Kushner would never have married Ivanka if she hadn't decided to change her religion for him.

Ivanka's father, Donald Trump, was unhappy about her decision. As Kushner himself detailed in his book, Donald asked him why Ivanka had to change religions, as opposed to Kushner converting for her. Andrea Bernstein's book "American Oligarchs: The Kushners, the Trumps, and the Marriage of Money and Power" also details Donald's reservations about the conversion. "Why couldn't she have married Tom Brady? Have you seen how far he throws a football?" he apparently lamented.

According to relationship experts, couples need to make time for regular date nights, as doing so is essential for a healthy marriage. However, it seems that Ivanka Trump and Jared Kushner didn't get this memo, with the twosome being all about the art of the deal. In fact, Trump told Vogue that her first date with Kushner was "the best deal we ever made."

As Trump explained to New York Magazine in 2009, a shared ambition and work obsession led to the pair falling in love. "I'm happy for him when he is in the office working late. I know how good that feels when you sit down and return e-mails," she said.

But it would appear that the couple struggles to see outside the world of corporate enterprise, with their dates ultimately proving to be work events rather than opportunities to unwind. "So, my husband's idea of a date night somehow always involves me looking at one of his development sites," Trump told Vogue. She recalled Kushner taking her out on a date in New York, only to end up on the roof of Whole Foods in the rain at midnight. "And he's showing me this giant site he just bought," she said. "I'm like, 'Huh. So this is why you chose that restaurant.'" Maybe Kushner's idea of romance is showing off his sizable property portfolio, but an inability to switch off and have a romantic date night is arguably a red flag.

The Trump family has been plagued by affair rumors throughout the years. Prior to dating Kimberly Guilfoyle, Donald Trump Jr. was married to Vanessa Trump. In 2011, Don Jr. reportedly cheated on Vanessa, who had recently given birth, with reality TV star Aubrey O'Day. While the saying "once a cheater, always a cheater" has been contested by couples therapists, Don Jr. would continue to be dogged by cheating rumors after he got with Guilfoyle.

Don Jr. started dating Guilfoyle in 2018, the same year he divorced Vanessa. For many years, they were quite the MAGA power couple, but in September 2024, Don Jr. was accused of cheating on Guilfoyle with socialite Bettina Anderson. The pair were snapped getting cozy in Palm Beach, and were apparently spotted kissing.

While Vanessa Trump allegedly threatened the woman Don Jr. reportedly cheated on her with, there were no such outbursts from Guilfoyle. According to insiders who dished to the Daily Mail, Guilfoyle had chosen to ignore her fiancé's alleged philandering. "Kimberly either didn't know about Bettina — or didn't want to know," a source said. "Did she hear whispers that Don Jr. was fooling around with someone else? Probably. She's no fool but it's easy to deceive yourself when you're so committed to someone and believe he's committed to you." The insider added that Don Jr. apparently doesn't feel the need to answer to anyone other than his father.

Kimberly Guilfoyle's relationship with Donald Trump Jr. has been eventful to say the least. During her time as Don Jr.'s right-hand woman, Guilfoyle has been through sexual harassment allegations, the Trump family allegedly shunning her, and screeching Republican National Convention speeches. But one thing Guilfoyle hasn't experienced is her fairytale Trump wedding.

Don Jr. proposed in 2021, though the engagement wasn't made public until the following year. "We're very committed and very in love," Guilfoyle told Jean Shafiroff, per Page Six. "He is my sweetheart. I already feel married and committed to him, 100%. Being his wife would be something that, of course, would be something that I think would be fantastic." As Vanity Fair pointed out, she hardly sounded over-the-moon at the prospect of becoming the second Mrs. Donald Trump Jr.

As the years pass by, Don Jr. and Guilfoyle still haven't tied the knot. There's a possibility that alleged animosity from the Trumps might be to blame for the absence of nuptials. In 2022, sources told Page Six that Don Jr.'s family weren't too keen on Guilfoyle. "The vibe is that the family doesn't like Kim," a source claimed. "She is trying too hard to be in the family." However, Eric Trump told the outlet that he's a big fan of his brother's fiancée. Also that year, Ivanka Trump shadily cropped Guilfoyle out of a photo taken at Tiffany Trump's wedding, further fueling speculation that the Trumps don't want Don Jr. to wed her.

For over two years, Tiffany Trump was in a serious relationship with Ross Mechanic. In 2018, it was revealed that the couple had parted ways at the end of 2017. Sources told Page Six that Trump, who was relocating from New York to Washington, D.C. to study at Georgetown Law, wanted to focus on her education. "I think it was hard for Ross to understand [that] Tiffany needs to put her future first," a source said. "She isn't dating anyone else, she is just really focused on law school, her studies and becoming her own person."

Despite Trump apparently telling her ex that she was focused on studying, as opposed to romance, she soon had another man in her life. In the summer of 2018, Trump was vacationing in Mykonos, Greece when she met Michael Boulos. Things quickly got serious between the two, and Trump even invited her new beau to spend Thanksgiving with her family. "Tiffany is happy she has so far been able to keep things with Michael under the radar," a source told Page Six. "But she introduced him to her family at Thanksgiving, and he comes across as a very intelligent young man from a great family." Though Trump and Boulos appear to have a loving relationship, one would be forgiven for side-eyeing the circumstances surrounding the pair's romance — not to mention how rapidly it advanced to the next level.

In January 2021, Michael Boulos and Tiffany Trump got engaged, but the former decided to put a ring on it in a rather unusual place. Boulos proposed to Tiffany at her father's workplace: the White House. In fact, he asked for Tiffany's hand in marriage the day before Donald Trump left the White House to make way for President Joe Biden.

The undoubtedly odd move from Boulos fueled speculation that perhaps there was a more sinister undercurrent to the proposal. Tiffany has always been in the shadow of her big sister, Ivanka Trump, who had long been dubbed the "first daughter." Perhaps the White House proposal was a means of Tiffany enjoying some of the limelight that Ivanka dominates.

Then again, Donald was facing a hefty backlash at the time of his departure from the White House, not only due to the contentious legacy he left behind, but his alleged incitement of the insurrection at the Capitol (the riots occurred mere weeks before Boulos proposed). Was Boulos' proposal a sneaky decoy from the bad press Tiffany's dad was receiving? Folks on social media sure seemed to think so. "Lmao at Tiffany getting engaged with just enough time to make sure she gets to have her engagement photo shoot at the White House while she still has access," podcaster and writer Gibson Johns wrote on X. Whether such assertions are true or not, proposing to Tiffany at the White House was, ultimately, more than a tad inappropriate.

Eric and Lara Trump's relationship got off to an awfully slow start. In a joint interview with Fox News, Lara recalled first meeting Eric while out with friends, joking that the pair immediately noticed each other as they were the tallest people in the room. "So, I was immediately intrigued and hopefully Eric felt the same way," said Lara. "It took us about three months to go on a date."

It may have taken a while for the couple to go on their first date, but it took even longer for them to tie the knot. "Eric wanted to make very sure ... so we got engaged five years and two days actually after our first date," said Lara. Eric added that Lara didn't put too much pressure on him to pop the question. While there's nothing wrong with wanting to be sure before getting married, it's undoubtedly odd that Eric was still uncertain whether he wanted to marry Lara after so many years together.

But perhaps there's another reason why it took Eric so long to put a ring on it. Rumor has it that Donald Trump never approved of Lara and wanted his son to marry someone else. "First and foremost, Donald didn't even like her for many, many years," Donald's former lawyer, Michael Cohen, claimed on "Political Beatdown" (via MeidasTouch). "He didn't want Eric to even marry her. He had found somebody else that was working at the Trump Organization that he wanted Eric to marry."

Eric and Lara Trump have been criticized for allegedly exploiting their kids for social media content, as well as using them as political tools. Giving a speech at the Conservative Political Action Conference (via X) in 2024, Lara revealed that every night she and her husband get their children to recite the pledge of allegiance as part of their bedtime routine. Her admission concerned social media users, with some claiming that the Trumps' bedtime routine was a red flag. "That's not the flex that she thinks it is," wrote one X user. "Imagine mentioning to friends or on a first date that you used to say the pledge of allegiance before going to sleep when you were young."

Elsewhere in her CPAC speech, Lara discussed the life lessons she and Eric are giving their kids. "I want [my son] to know that it's okay to be a patriot, it's okay to love god, and it is okay to grow up into a strong, masculine man," she said.

In 2022, Lara was condemned after sharing an example of how she was teaching her son about masculinity, posting an Instagram video that showed the youngster driving a toy car in the midst of Hurricane Ian. "Thought we had a clear window, turns out we did some character building instead," she wrote. When her son, who looked uncomfortable in the pouring rain, protested that he wanted to stop, Lara replied, "No, you can do it. Let's go."