A Full Timeline of Miley Cyrus and Maxx Morando’s Low-Key, High-Cute Relationship Now That They’re Engaged

Living legend Miley Cyrus and songwriter/producer/drummer Maxx Morando have been a confirmed item for over four years...and it seems they’re ready to take their relationship to the next level. After they showed up at the Avatar: Fire and Ash premiere (with Miley notably sporting a new diamond ring on *that* finger), a source for Page Six confirmed the two are now engaged (!!).

If you’re new here (“here” being their relationship), don’t worry about it. We put together a timeline just for you—yw! Prepare to find out exactly how these two met and moved in together, and try not to be too jealous of their hair (which we can all agree is full of secrets).

September 2021

Miley name-drops Maxx during an interview about her ~festival wardrobe~ with Vogue, saying, “This look is a one-of-a-kind collaboration between two of my favorite emerging artists, Maxx Morando and Shane Kastl. Their collaboration is the perfect example of sustainability becoming the next fashion phase, and it proves that anything can be reinvented, which resonates with me deeply.”

No one thinks anything of it at the time, BUT THEY SHOULD HAVE.

November 2021

Miley and Maxx are photographed together at a Gucci event, and this handhold makes it pretty clear they’re a couple:

March 2022

It takes several months of “ummmm these two are obviously dating” before an Us Weekly source confirms Miley and Maxx are fully a couple.

“It’s a new relationship,” the insider says. “They’re still getting to know each other at the moment. They are having fun and have been spending a lot of time together.”

April 2022

Miley and Maxx are spotted kissing in L.A.:

December 2022

After keeping their relationship private for most of 2022, Miley and Maxx are seen grabbing dinner at Nobu.

March 2023

A couple months later, Miley shows up with Maxx at the Versace show in West Hollywood, and they’re seen holding hands:

That same month, Maxx casually reveals he worked on Miley’s album, Endless Summer Vacation:

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And soon after that, a source tells People that Maxx “has no interest in being a huge celebrity; he’s very low-key. Miley loves these qualities. Miley can be herself. They are supportive of each other’s careers. Miley is enjoying life and things are great.”

May 2023

Miley opens up about meeting Maxx to Vogue UK, saying, “We got put on a blind date. Well, it was blind for me and not really for him. I thought, The worst that can happen is I leave.”

She also reveals her ringtone for him is “Tyrone” by Erykah Badu, saying, “I call that ‘boyfriend sexy ringtone.’”

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December 2023

Us Weekly pops up with another source who tells everyone, “Miley could see a healthy, positive, and fruitful life with Maxx. She’s learning from her past marriage and relationships and wants to build toward a better future with him.”

February 2024

Miley thanks Maxx (aka “my love”) during her Grammys Record of the Year speech:

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And they share a cute kiss!

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And soon after, People drops the news that Maxx and Miley are living together, with a source saying, “She is very happy with him. Miley has changed a lot in the past couple of years. She seems more calm and harmonious. Everyone loves Maxx. He’s a great guy. She is very happy with him. He’s private and doesn’t like being in the press. It’s been good for her.”

Ofc, Us Weekly comes through with its own report confirming that Miley and Maxx are living together. The Us Weekly source’s musings? “Miley owns a number of properties, but she and Maxx recently moved in together and are staying at her home in Malibu. It’s a huge mansion overlooking the water in a gated community.”

The insider adds that Miley and Maxx “spend a lot of time on the private beach together” and that the drummer “had been staying over there a lot with Miley because they spend so much time together. But they recently made it official, and he moved in.”

November 2024

Miley graces the cover of the Harper’s Bazaar Art Issue, where she gives rare insight into her relationship with Maxx.

“He’s very similar to me. We just don’t take life too seriously,” she adds, going on to explain that she worked with Maxx on her upcoming album: “I worked with my dad forever. That’s how me and my ex-husband met each other. I’ve always worked with the people that I love. And Maxx just inspires me so much.”

February 2025

Maxx accompanies Miley to the 2025 Grammys!

And few weeks later, they attend SNL50 together:

March 2025

Maxx pulled up to the Oscars with Miley, and they looked SO good.

Oh, you thought they were done? They also attended Vanity Fair’s Oscars party, complete with baby bangs and an outfit change.

June 2025

Another cute sighting/great hair alert:

September 2025

In an interview with The Cut, Miley offers more insight into her ‘ship with Maxx, explained how her mom had previously always encouraged her “to stay with the wrong guy because they’re hot.”

She continued, “No, I ended up with a person who means a lot to me and treats me really well and respects me. I had to learn that the hard way because my mommy taught me the wrong way, and then I had to learn the right way by myself.”

December 2025

Miley and Maxx hit up the L.A. premiere of Avatar: Fire and Ash, and fans quickly clock that Miley seems to be sporting a new jewel on her left ring finger. I mean, it’s hard to miss:

Soon after, a source for Page Six confirms that Miley and Maxx are, in fact, engaged. We love to see it!!

That’s all for now, but we’ll keep you updated on the latest with Miley and Maxx, in case you find yourself feeling invested.