Miley Cyrus once proclaimed that she needed an older man (or woman) in her life, but she threw that all out the window for her boyfriend, Maxx Morando, with whom she shares a considerable age gap. But before we recap the highlights of Cyrus and Morando’s romance, which has been going strong for years, here’s the singer’s previous stance about age in relationships. “That’s why I’m looking for an older man,” she shared on Joe Rogan’s podcast in September 2020. “I don’t need a man or a woman that’s going to take care of me — because I’ve got money. I’ve got all the things I need to take care of myself.” She continued, “I need them to be able to take care of them.”

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Of course, people are allowed to change their minds, and that’s exactly what Cyrus did when she started dating the younger musician, who was born on November 16, 1998. As of June 2025, he’s steadily heading toward 27. Meanwhile, his older girlfriend is also a ’90s baby — just an early ’90s baby. She was born on November 23, 1992, meaning that, sans those crucial developmental years the brain seems to toss out of our memories, she probably remembers at least half of what people have referenced as one of the last great decades. Morando, on the other hand, probably references the early 2000s when citing his earliest memories. And despite their 6-year age gap, the couple seems to work for various reasons!

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Miley Cyrus used to be an open book about her previous relationships (like Cyrus’ exes, who have had plenty to say about her), but she hasn’t been nearly as public about her relationship with Maxx Morando as she has been about previous suitors. That said, she’s shared little tidbits about how their celebrity age-gap romance came to be. “We got put on a blind date,” shared Cyrus with Vogue in May 2023. “Well, it was blind for me and not really for him. I thought, ‘The worst that can happen is I leave.'” Obviously, Cyrus gave love a chance by not ditching her future beau before he showed up — and the rest is history.

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As for how their age gap affects their romantic dynamic? “He looks at life really differently than I do,” she previously shared with Harper’s Bazaar. “He grew up with a laptop. I had a desktop computer that I shared with my brothers and sisters.” Their six-year gap has also led to some interesting differences when it comes to raising their fur baby. “Honestly, he’s raised our dog off Reddit,” she continued, adding, “I’m like, Are you sure we’re supposed to be doing this? And he’s like, On Reddit it says blah, blah, blah.” Overall, however, “He’s very similar to me. We just don’t take life too seriously.”