Red Flags In Miley Cyrus And Maxx Morando's Relationship From Our Matchmaker

Pop star, certified Disney Legend, and style icon Miley Cyrus has undergone a serious transformation in the spotlight for almost two decades. And apart from seeing her grow up, we've also gotten to witness the star fall in and out of love. Since late 2021, Cyrus has been dating musician Maxx Morando, the drummer in the band Lilly, and while they've been very private about their romance, we've gotten to see glimpses of their happy relationship from time to time.

That said, we know better than to trust what's served to us, which is why we reached out to Susan Trombetti, matchmaker and CEO of Exclusive Matchmaking. Exclusively for Glam, Trombetti dove deeper into the couple's relationship. "When it comes to Miley and Maxx, not a lot is known about their relationship because they do tend to keep it private," she tells us. "For Miley, this is a good thing because too much of her life has been in the public and full of turbulence. There has been lots of drama in her life, and while you can only hope for the best for them, you can't help but worry for her." While Trombetti points out that the relationship between the two musicians seems to be doing fine, she adds, "There are numerous red flags that jump out at me, though." And once she said that, we knew we needed to know more.

One thing that even Miley Cyrus has addressed is the six-year age gap between herself and Maxx Morando. While that type of age gap usually doesn't mean a lot, the former Disney star admitted that her Gen-Z boyfriend often surprises her with how different from her he is. "He looks at life really differently than I do," Cyrus told Harper's Bazaar in November 2024. "He grew up with a laptop. I had a desktop computer that I shared with my brothers and sisters."

Susan Trombetti points out their age gap as a potential red flag since the two are at different stages of their lives. "Maxx is only 26 years old. Miley grew up early, but most don't. He has been with her for a few years now," Trombetti tells us exclusively. "I don't think people should make a very long-term commitment until they have lived through their twenties." 

Moreover, the matchmaker stresses that Morando undoubtedly still has some growing up to do since he entered the relationship in his early 20s. "She is ready and grew up quickly, which means it could be another heartache for her down the road," Trombetti explains. "He has been dating her since he was 23, if not a little younger. That's very serious at a young age."

Those who have been keeping up with Miley Cyrus over the years know that there's been quite a bit of drama in her family following the divorce of her parents, Billy Ray Cyrus and Tish Cyrus, in 2022. The former couple's children chose sides, and for Miley, this meant standing alongside her mother. In fact, Miley didn't even thank her father when accepting her first Grammy Award despite Billy Ray playing a major role in his daughter's career, as well as her love of music.

Now, while odd and dysfunctional family dynamics aren't uncommon, Susan Trombetti explains just how they could negatively impact Miley's romantic relationship. "Her family life seems a bit dysfunctional, which means she didn't have a good support system or role models, causing her not to know what a good relationship looks like," Trombetti shares exclusively with Glam. "While I am sure she loves them, her family doesn't seem to be good role models for a relationship. Billy's focus seemed to be on living his dream vicariously through her, and so that husband and wife relationship couldn't have been a good role model for her." 

Trombetti adds that due to Miley's family dynamics, she might end up putting too much pressure on Maxx Morando. "I am sure she loves her family, but it's hard for her to find stability. She may depend too heavily on him," the matchmaker tells us. In fact, supporting your partner when they have a toxic family dynamic is never easy.

It's no secret that celebs often date other celebs since they know what they're getting into. While Maxx Morando is a talented musician, his fame is currently nowhere near Miley Cyrus' level, which could have a negative effect on their relationship. A source close to the couple revealed to ET in March 2022 that Morando's private lifestyle is what drew Cyrus to him. "Miley likes the fact that they are low-key as a couple and is just focused on doing her thing and being around people that make her happy, and Maxx does that," the insider said. Similarly, a source told People in March 2023 that Morando is all about keeping his life private: "He has no interest in being a huge celebrity; he's very low-key."

Of course, when you're dating an international pop star who's been in the game for almost two decades, keeping a low-key life isn't easy, and this is exactly what Susan Trombetti points out as a potential red flag in the couple's relationship. "The scrutiny that comes with being a star — much less all the scrutiny around Miley — is intense on their relationship," she tells us exclusively. "He is very private, and it's all out there usually with Miley."

We've all heard that opposites attract, but in reality, being too different from your partner isn't ideal — and there are numerous signs that you and your partner are too different. Speaking to E! News in January 2022, a source revealed that Miley Cyrus and Maxx Morando share common interests. "They are both artistic and creative, so they bond over being musicians," the insider said. However, it doesn't take an expert to realize that there are also plenty of differences between the two — namely that Morando seems shy and private, while Cyrus has always been a loud and energetic open book.

"Their differences in personalities might create discomfort for Maxx," Susan Trombetti tells us exclusively. "There is a lot of pressure on Maxx dealing with someone that isn't as private. She speaks her mind, and she is fierce and such an enormous talent because of it. Their differences, which could be a good thing, could also drive them apart." This isn't an issue that can sit on the back burner, either. In fact, Trombetti concludes that she's "sure" that "[i]t's something they navigate."

Now, if you love celebrity relationships and the juicy drama they bring, check out all the red flags in Kelly Ripa and Mark Consuelos' relationship.