Red Flags In Ivanka Trump And Jared Kushner's Marriage From Our Matchmaker

Socialite, two-time first daughter, and occasional politico Ivanka Trump has been dragged over a lot of issues, from the serious to the inane. When the public isn't giving side-eye at Ivanka Trump's most inappropriate outfits or pinpointing the Trump heiress' biggest makeup mistakes, they might instead be digging deep into her financials and business practices. Basically, there's a lot to unpack in Ivanka's life, including some strange, red-flag aspects of her marriage to Kushner.

In 2022, an anonymous source purportedly told Radar Online, "It's all falling apart. ... They're always fighting and can barely contain their growing animosity for each other even when they appear in public." While Jared and Ivanka still haven't divorced or even admitted to rocky patches in the years since, it makes us wonder: How healthy is their marriage, really?

For deeper insight into the duo's relationship wellness, Glam spoke exclusively to Susan Trombetti, matchmaker and CEO of Exclusive Matchmaking. "When it comes to red flags in Ivanka and Jared's relationship, frankly, I am surprised they are still together," says Trombetti. "It's not that they are a bad couple with a lot of dysfunction, it's just that there is a lot to break down here with what has to be major impacts on their marriage." Specifically, Trombetti explains that Jared and Ivanka's partnership has to weather social stressors on all fronts, from family drama and social isolation to perpetual media attention.

When it comes to marriage, integrating two families is always a little bit of a minefield. Even if you're not dealing with toxic in-laws, it can take a lot of finesse to dovetail your worldviews, traditions, and lifestyles. This isn't any easier for celebrity couples like Ivanka Trump and Jared Kushner; regarding Kushner's relationship red flags, Susan Trombetti responds, "Can I just say his in-laws?"

As Trombetti points out, the Trumps' ever-increasing fame and infamy probably puts a lot of pressure on Jared and Ivanka's marriage. The matchmaker exclusively told Glam, "Let's face it, Donald Trump must be all they lived and breathed. They campaigned for him, worked as senior advisors at the White House, and unfortunately, were caught up in the legal drama, which had to be scary."

Burnout from this intense, in-law-centric role may be one reason that Jared Kushner won't be taking on any official roles in Donald Trump's second administration. "Both my wife and myself were working in the White House, which is a 24/7, high-stakes job," Kushner told Axios in February 2024. He noted, "I've really enjoyed the opportunity [in the years since] as a family to be out of the spotlight." When pressed, Kushner affirmed that he'd turn down any job offered to him by his father-in-law — but only time will tell if maintaining some professional distance from Donald will help promote better balance and calm in his relationship with Ivanka.

Jared Kushner isn't the only one who has to navigate the waters of the Trump family carefully. Even Ivanka Trump herself has to play nice amidst internal drama, particularly around her relationship with her stepmother Melania Trump — a strain that could affect both Ivanka's personal happiness and her wedded bliss. Reflecting on Jared and Ivanka's relationship, Susan Trombetti observes, "The stepparent relationship with Melania must impact both of them."

As revealed in "Melania and Me" by Stephanie Winston Wolkoff, the then-first lady's former senior advisor, the friction between Melania and Ivanka escalated into a game of social and political chess. For instance, Melania reportedly put her team to work on a scheme called "Operation Block Ivanka" to keep her stepdaughter from taking center stage at the presidential inauguration in 2017. Another biography of Melania Trump, "The Art of Her Deal: The Untold Story of Melania Trump" by reporter Mary Jordan, illuminated more telling details of this purported feud: Melania apparently calls Ivanka "The Princess" for her spoiled and entitled attitude, while Ivanka calls Melania "The Portrait" because she so rarely speaks.

Yikes — the Trump women clearly have a lot going on behind the scenes. "I am not saying Melania is an evil stepmother, but it's the classic troubled relationship between stepparent and child," Trombetti exclusively tells Glam. "I am sure it bothers Ivanka, and then she drags that back home into their marriage." To help mitigate this red flag and protect their own family life, Jared Kushner will have to be a strong pillar of support for his wife — and maybe investigate a few ways to support a partner with a toxic family dynamic.

During the last few elections, some outlets have noted that politics has become especially aggressive and polarizing. This has gone beyond the polling booth, driving rifts into families, communities, and even friend groups. Case in point: Being associated with the Trump political machine has apparently ostracized Jared Kushner and Ivanka Trump from some former allies. "It is said they lost friends over Donald Trump," Susan Trombetti exclusively reveals to Glam. "The loss of friends due to the presidency has to be hard on them."

You might think that Kushner is in a particular position to resent that the behavior of his in-laws is impacting his social life, but he has taken a curiously callous view of his friends' exodus. "I call it an exfoliation," Kushner told Forbes. "Anyone who was willing to change a friendship or not do business because of who somebody supports in politics is not somebody who has a lot of character." Instead, Ivanka seems to be the one reeling most from the loss of close friends. Her childhood gal pal Lysandra Ohrstrom even penned an essay for Vanity Fair explaining how Ivanka has made herself persona non grata. "Self-proclaimed former friends vow that Ivanka can never show her face in Manhattan again. ... She really will never recover from the decision to tie her fate to her father's."

Trombetti acknowledges that some of these lost friendships may have been built on a shallow foundation to crumble so readily. "Anytime someone distances themselves over others' actions, were they ever really your friend? Probably not, but it still must be hard for them to feel shunned." Unfortunately, being with someone who doesn't have close friends can trigger codependency, among other undesirable effects. So this social isolation is an emotional obstacle that Ivanka and Jared will have to overcome together, not just for their individual happiness, but for their overall relationship health.

We've addressed the difficulties of media scrutiny many times before, from red flags in Justin and Hailey Bieber's marriage to red flags in the partnership between Ryan Reynolds and Blake Lively. As Susan Trombetti says of such attention, "It's always a bad thing for a couple, whether it's in their public or personal lives." Unfortunately for Ivanka Trump and Jared Kushner, the pressure point of intense media scrutiny also applies to their romance — and in spades.

"They are being bothered a lot," Trombetti exclusively tells Glam. "They seemed to prefer a private life, even though that's hard when you are in the Oval Office as senior advisors. [Ivanka's] father is president again, so of course, that's going to spill over to her personal life, even though they aren't as involved this time."

Ivanka has expressed unhappiness over the publicity of politics — so much so that, like her husband, she has decided to separate herself from Donald Trump's second administration. "This time around, I am choosing to prioritize my children and the private life we are creating as a family. I do not plan to be involved in politics," she reportedly wrote in a social media statement at the outset of her father's 2024 campaign (via Business Insider). This is likely a step in the right direction for the sanctity of Ivanka and Jared's relationship, though we doubt they'll ever be low-profile individuals. In addition to taking a backseat during Donald Trump's second presidency, Jared and Ivanka will probably need strict boundaries to preserve their marriage in the face of constant media attention.

It's not unreasonable to want to be your spouse's number-one person. For Jared Kushner, though, this could be a tough ask — his wife Ivanka Trump has a notoriously close relationship with her father. "Ivanka is a daddy's girl. There is no question here," Susan Trombetti exclusively tells Glam. "Being a daddy's girl can create conflict. ... the 'Princess' nickname from Melania is probably well-fitting, given that she will always be Donald's princess. That's a lot for Jared."

Speaking of a lot, there are also the times that Donald Trump has publicly — and borderline creepily — blurred the lines of his affection for Ivanka. "I've said that if Ivanka weren't my daughter, perhaps I'd be dating her," Donald famously told The View in 2006. And in 2015, he told Rolling Stone, "She's really something, and what a beauty, that one. If I weren't happily married and, you know, her father...." Shudder. As uncomfortable as these tone-deaf comments sound to uninvolved third parties, they must be all the more difficult to bear from your father-in-law, and about your wife.

In this sense, it may be extra important that Jared and Ivanka are putting some space between themselves and Donald Trump during his second term. Beyond easing the pressures of visibility and constant contact with in-laws, a little private, family-oriented time could help Jared and Ivanka deepen their relationship without the looming shadow of Daddy Dearest.