Trumpland doesn’t have a great track record when it comes to relationships. Take their boss, Donald Trump, for example, who got married not once, not twice, but three times – the only U.S. President with that kind of marital history. His third marriage to Melania Trump is also not all rainbows and sunshine, as it seems.
Divorce rumors just keep piling up for the President and his First Lady. Meanwhile, Vice President JD Vance and his wife, Usha, also deal with a fair share of separation rumors every day.
They are not the only ones. Karoline Leavitt, who holds a very pivotal position at the White House as Trump’s Press Secretary, is often a subject of online gossip, especially because of her massive age gap with her husband, Nicholas Riccio. Seriously, is there anybody in Trumpland who has a solid relationship? Experts shared their opinions, and you would be surprised.
While Donald Trump and Melania absolutely don’t embody the picture-perfect couple, Susan Trombetti, the CEO of Exclusive Matchmaking, says, “They are great partners.” In an interview with The List, the matchmaker noted, “Romance doesn’t seem to be at the top of the list for these two. It’s about Barron, family, and politics. The relationship seems to work well for what they both need.”
The same also applies to JD and his Second Lady. Trombetti says, “This relationship appears to be a struggling romance, but definitely a partnership. They have had some public quarrels … He’s the VP, they have younger children, and it’s hard. She is definitely supportive.” However, she warns, “but it’s wearing thin.” So far, the rumor goes, this is what we expected about this couple’s relationship as well.
New piece I’ve been dying to write for eons now. JD and Usha Vance seem to hate each other, and barely bother to conceal it.
This is no way to live your life. But JD Vance wants this misery for everyone. https://t.co/oH8tbmlDdk
— Amanda Marcotte (@AmandaMarcotte) August 11, 2025
Meanwhile, regarding Leavitt and Riccio, the matchmaker had to say that even though their marriage seems to be working now, it may not have the staying power, noting that “eventually life stage issues could be a problem,” due to their 32-year age gap.
So, which couple in this group has the best solid grounding when it comes to their relationship? According to the expert, it’s actually Donald Trump Jr. and his new girlfriend, Bettina Anderson. They were first linked in September, around the same time when Don Jr. and Kimberly Guilfoyle went their separate ways. In January, during his father’s inauguration, Trump Jr. went public with his model and socialite girlfriend, and their relationship has been getting a lot of public attention since then.
Donald Trump Jr. and girlfriend Bettina Anderson can’t resist excessive PDA before President Trump’s arrival https://t.co/jpSuaRpZw3 pic.twitter.com/Q3LrTpY4lj
— Page Six (@PageSix) July 13, 2025
Susan notes that they “might have best relationship and romance going because it’s new, they don’t have a lot of marital responsibilities, or mutual children.” However, that said, she also adds, it’s all about Romance with Bettina. With Kimberly, on the other hand, “he definitely had a great partnership.”
