The Glaring Red Flags Karoline Leavitt And Her Husband Won't Last

Unlike Hollywood, where every other couple is branded "relationship goals" until the inevitable breakup post drops, political power couples more often raise suspicion than attract stans. From what appears to be a stiff dynamic between Ivanka Trump and Jared Kushner to even the decades-long romance of Barack and Michelle Obama, spectators almost always spot red flags. This is especially true for Karoline Leavitt and Nicholas Riccio, whose massive age gap alone will make you doubt their entire relationship.

But you'd never guess that from how the White House press secretary talks about her husband, although she was smart enough to acknowledge that their relationship is anything but conventional. "It's a very atypical love story," she said in a "The Megyn Kelly Show" appearance. "He is my greatest supporter, he's my best friend, and he's my rock. He's built a very successful business himself, so now he's fully supportive of me building my success in my career."

But it's not just the age difference that could spell trouble — even relationship experts think so. From clashing life stages to conflicting personalities, the red flags on their romance keep stacking up — even if everything seems fine on the surface. Here's a closer look at why this pairing might not be as picture-perfect as they appear, and what experts say about their chances.

Karoline Leavitt is someone who is unapologetically proud of her faith. She wears her Catholicism on her sleeve — and on her neck (literally). The devout Catholic is known for praying before media appearances and proudly rocking a cross, no matter what her haters say. But her public embrace of religion has also made her a target, especially when her personal life, particularly her marriage to Nicholas Riccio, became tabloid fodder.

Critics zeroed in on the timeline of their relationship, pointing out that the couple got engaged around the same time she became pregnant — and had their baby before officially tying the knot. "It was a shotgun wedding, too. I read they got engaged on Christmas Day 2023. Baby was born July 2024. I'm doing the math, and the timing of the engagement would be several weeks after finding out," one critic pointed out on X, formerly Twitter. "He got her pregnant. They had a shotgun wedding, because that's what her circle demands when you get caught having premarital sex," another remarked on Reddit.

Leavitt, of course, stood firm, defending both her relationship and the authenticity of their story. Speaking on "The Megyn Kelly Show," the press secretary swears their love story isn't a scandalous slip-up but a genuine connection that started as a friendship. "A mutual friend of ours hosted an event at a restaurant that he owns up in New Hampshire and invited my husband," she recalled in the interview. "I was speaking. We met, and we were acquainted as friends. And then we fell in love."

Karoline Leavitt doesn't seem to be bothered by the fact that Nicholas Riccio is quite literally old enough to be her father — or maybe even her grandfather, depending on who's counting.  "It's a very atypical love story, but he's incredible," she told Megyn Kelly, brushing off the 32-year age gap like it's nothing. And sure, there are May-December romances that stand the test of time, but relationship experts aren't exactly rushing to romanticize the dynamic. Susan Trombetti, matchmaker and CEO of Exclusive Matchmaking, said the age gap shouldn't be shrugged off that easily. 

"Some of the cons are that he is slowing down in this stage of life and is ready to have a partner beside him as her career is taking off. It's a definite mismatch," she exclusively told Nicki Swift. "I have had clients coming to me that divorced because they married someone so young, and they were no longer compatible. He wanted to travel and retire, and her career was soaring. I see that as a possibility here as well."

That said, Trombetti still offered a glimmer of optimism. Maybe Riccio's cool with just having a supportive role, especially now that there's a baby in the picture. "I don't know a lot about their child, but her husband could be the primary caretaker so there is a benefit that negates the con of having children too late in life," she added. "It's definitely working for them now, but will it always? Who knows?" Perhaps only time — and a good prenup — will tell.

Being generations apart is one thing, but having opposing personalities is a whole other story. According to Karoline Leavitt herself, they have the textbook "opposites attract" kind of relationship, and she's not shaming her husband for being different from her. In fact, she thinks it's part of the charm. "He's an introvert (complete opposite of me)," she proudly told her Instagram followers and went on to gush about how that doesn't matter at the end of the day. "I respect his privacy on here — but he's my number one fan, the best dad, and just the best man I've ever met."

But Susan Trombetti isn't buying it easily. She sees the combo of extreme personality differences and a significant age gap as a recipe for trouble. "Karoline Leavitt is not even out of her twenties and is married to a man who is almost 60. I don't think anyone should ever marry before they experience their 20s," Trombetti told Nicki Swift. "That said, she did marry him, but I think there is more to it than they are just opposites. They are on the precipice of different life stages. This could create more problems than generational differences due to the extreme age gap."

That said, Trombetti is not being totally dismissive of their marriage — and even noted that Leavitt probably knows what she's doing even though it may not always appear that way. "Some benefits could be that she has more stability, connections, and wisdom from being married to someone older," she continued. "I am certain she probably loves him very much and she is not a trophy wife. She is bright, determined, and intelligent as well as ambitious."

And then there's also the not-so-small issue of their careers. Karoline Leavitt is practically the face of the White House as its press secretary, while Nicholas Riccio runs a real estate empire. While Riccio presumably has more wiggle room in his schedule given that he owns his business, Leavitt doesn't have the same kind of flexibility — at least not right now. And per Susan Trombetti, that kind of career imbalance can strain any marriage — especially when it's layered on top of a hefty age difference.

"I see her increasingly prominent role in the administration as more of her career advancement. In this administration, it's only 4 more years, so there is time to reconvene and come back together as a couple if it takes her away from the relationship too much now," Trombetti explained to Nicki Swift, adding that if the couple wants to make things work, compromise is key. "Every couple needs to negotiate this in their own way. It remains to be seen. At the end of the day, they are dealing with more of a big age gap that threatens them more as a couple than her rising star within the Trump administration."

Still, if Riccio feels like he's being overshadowed, he's doing a great job of hiding it. According to Leavitt, he's nothing but supportive. "He's the father of my child and he's the best dad I could ever ask for," she gushed to Megyn Kelly. "And he is so supportive, especially during a very chaotic period of life ... I say, 'I walked into your life, and it's been a circus ever since,' but God bless him because he's fully on board."