Miley Cyrus’ Dating Drama: From Nick Jonas to Maxx Morando

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Miley Cyrus has packed a lot of life into her 32 years.

She’s spent some of it single, her comfort being on her own admittedly hard-fought.

After her split with Patrick Schwarzenegger in 2015, which caused a significant resurgence of nostalgia when they encountered each other at the Met Gala on May 5, she expressed to TIME that she had finally grown comfortable with solitude.

Miley doesn’t shy away from companionship, as her dating experiences with both men and women have provided numerous chances for love throughout the years. With a diverse range of relationships, some brief while others more serious—like her long-term, on-again, off-again relationship with Liam Hemsworth, lasting a decade—she has gained a deeper understanding of her current situation.

Miley explained to her fans on May 6 during a Spotify-hosted preview of her new album, Something Beautiful, that when her house caught fire in 2018, not only did it burn down but many of her relationships were affected as well. She went on to say that this difficult experience ultimately led her to discover even more magic and feel an immense sense of gratitude.

Miley mentioned that if she could talk to her younger self, she would advise her to value those difficult times, as they are guiding her towards the light.

And when there’s light, the flowers bloom.

For quite some time, the Grammy-winning artist has been finding a striking resemblance between herself and Maxx Morando, who is known as the drummer of Liily at the age of 26, and she often refers to him as being remarkably like her.

She expressed to Harper’s Bazaar last fall that she tends not to approach life overly seriously, but while she labeled herself as “purposely vague” and “highly inconsistent,” she does follow a pattern of collaborating with those she cherishes. Moreover, Maxx serves as a significant source of inspiration for her.

As a die-hard fan, I can confidently say that Miley has been through the ups and downs of love like no other, but one thing remains constant – her pursuit of joy. She’s wisely understood for quite some time now that authenticity to who she truly is, lies at the heart of her happiness.

Here is a look at the dating history that brought Miley to this place and time:

Following Miley Cyrus’s rise to fame as Hannah Montana at the tender age of 13, she encountered her first love with another Disney Channel sensation, Nick Jonas. This is as per her account in her 2009 autobiography “Miles to Go,” where she noted that June 11, 2006, marked the day they first met at a charity event.

Miley stated that although they didn’t make their venture public, it was a genuine operation even though the participants were not old enough to have driver’s licenses at the time.

She shared with Seventeen magazine in 2008 that they officially became a couple the moment they first met. He had been pursuing her, and he declared, “I find you attractive and I really enjoy your company.” To which she responded, “Oh my goodness, I really like you too!

She went on to say, “Nick and I shared deep affection for one another, and that hasn’t changed. However, we were deeply in love during those years. He was a constant presence in my life, almost 24/7. But maintaining the secrecy of our relationship proved challenging. We often clashed, and it wasn’t a particularly enjoyable experience.

Back in late-2007, when the breakup hit, I couldn’t help but weep for an uninterrupted month. The sorrow that engulfed me was immense. I found myself slipping into a strange melancholy, and as a coping mechanism, I decided to transform my appearance by dyeing my hair black.

During that period, she didn’t reject the possibility of marrying Nick or starting a new relationship again. In an interview with the magazine, she expressed, “Since then, I’ve encountered numerous wonderful men, but I enjoy being the independent woman who isn’t tied down.” She added, “No one can claim me, and I don’t let anyone get close. I’m free, and I find it attractive to be self-reliant.

Moreover, dating is enjoyable too, as Miley began seeing model-actor Justin Gaston in 2008 following their introduction by her father on the set of Hannah Montana, after he had appeared as a contestant on Nashville Star hosted by Billy Ray Cyrus.

In 2009, when asked about the four-year age difference between her and Justin (who was 20 at the time), she stated to Glamour magazine, “I don’t feel like I’m doing anything wrong, and I’m prepared for people to accept it.

Her fans were overjoyed on her behalf, she noted. “To be honest, it’s been a while since I’ve felt this level of happiness…with all the hard work, moving from Nashville to L.A., enduring a tough breakup. Now, I’m back to feeling happy once more, and I believe this newfound joy is evident in my music and my projects. frankly, I don’t feel like there’s anything I need to conceal anymore. And the truth is, I adore him immensely, so much so that I don’t worry about it too much.

Miley referred to Justin as her “closest friend,” but following approximately nine months together, they parted ways when she was set to shoot a movie titled “The Last Song” over the course of two months in Savannah, Georgia.

The Last Song turned out to be only the beginning for Miley and Liam Hemsworth.

By the wrap-up of the 2009 film shoot, costars were also exchanging goodbyes off-screen with a kiss, and they officially walked the red carpet together for the first time as a couple at the movie’s Los Angeles premiere on March 25, 2010.

Miley mentioned to People that she isn’t particularly affectionate by nature. She isn’t sentimental or ‘mushy’. It was Liam who sparked her desire for a genuine romantic connection.

In May 2012, an Australian actor put forward a proposal, but their engagement was terminated in September 2013, shortly following Miley’s MTV Video Music Awards performance which suggested that maybe she could not be domesticated.

Or at least that she couldn’t stop, wouldn’t stop just doing her own thing.

She said to ABC News’ Barbara Walters in December 2013 that she never wants to depend on someone again, feeling as though without them, she cannot express her true self. She might consider getting married someday, but she clarified, ‘I got engaged at 19 and I wouldn’t change that experience. It was great to sport a large ring for some time. Now, however, I feel like I can truly be content on my own.’

Despite parting ways romantically, Miley and Liam continued their friendship. In fact, as Miley shared with Elle U.K. back in September 2015, they remained extremely close and cherished each other deeply.

At that point, she confessed that she often felt significantly more mature than someone at 22 years old. She emphasized that this didn’t mean she believed herself superior to others her age, but rather it was due to the fact that most of her friends were in their thirties and she had spent her formative years on a TV show surrounded by adults. As a result, she found herself drawn towards Liam, as it was refreshing to be with someone close to her own age.

In 2014, Miley Cyrus began dating USC student and entertainment family member Patrick Schwarzenegger. This relationship allowed the “Party in the USA” singer to socialize with people her age and experience some aspects of college life – particularly the football games.

Although the actor from White Lotus is currently engaged to Abby Champion, it seems he wasn’t ready for a long-term commitment back then. Pictures of him appearing close with another woman during his spring break trip to Cabo in 2015 reportedly led to his split with Miley Cyrus, despite his claims that no improper behavior took place.

Wow, it’s one of my closest friends who is dating someone else,” Patrick posted earlier. “I would never act in a way that goes against my girlfriend.

It wasn’t too shocking that Miley Cyrus, who openly discusses her fluid sexuality, was involved in a romantic encounter with model Stella Maxwell in 2015.

Miley stated to Elle UK last September that she is 22 and goes on dates, but her style changes every fortnight, not only the people she’s seeing. She praised Stella but noted that once you spend time with someone, you’re often labeled as being in a relationship. However, she added, just because I’m dining with someone doesn’t mean they’re necessarily a date.

Miley was also more focused than ever on her relationship with herself.

In an interview with TIME in May 2015, she shared that there have been instances in her life where she’s had romantic partners. However, she also enjoys spending time alone and not sharing herself with someone else. She believes this is a newfound freedom for women, something she doesn’t think her mother could have experienced at her age. She emphasized that her future doesn’t hinge on having a partner.

2015 marked the revival of Miley Cyrus and Liam Hemsworth’s romance, which had been a topic far from chemistry-related issues. By year’s end, they were once again engaged.

Or:

Their love story didn’t involve any chemistry complications. Towards the close of 2015, Miley Cyrus and Liam Hemsworth rekindled their relationship. Not long after, their engagement was on again too.

As a dedicated follower of Miley, I can say that she has always been transparent about her feelings regarding marriage. Back in September 2017, when speaking with The Sun on Sunday, she made it clear that she wasn’t in a hurry to walk down the aisle. She expressed, “I’m just going along for the ride. In some relationships, you can lose yourself by being with someone else. However, my relationship has helped me discover more about myself. I have no idea what the next few years hold, but if it’s possible to become even happier, then I’m all for it.

One truly never knows what the future holds.

On December 23, 2018, Miley and Liam held a poignant wedding ceremony. This joyful event took place just under two months after they had tragically lost their Malibu home to the Woolsey fire, an incident that burned down over 1,600 structures in the vicinity.

Miley expressed to Elle months ago that she finds her marriage situation confusing for others. However, she emphasizes that her relationship is unique and complex, perhaps beyond the understanding of many people at this time due to its modern nature. She also mentioned that she might not make her relationship public because it’s so different from traditional norms. Moreover, she clarified that she doesn’t conform to a typical wife role and even dislikes the term ‘wife’.

She mentioned that she might have been involved in a straight relationship, yet she found herself strongly drawn to females sexually.

The interview appeared on July 11, 2019. A month after that, news about their separation emerged, with Liam filing for divorce shortly afterward.

Miley stated on her “Used To Be Young” TikTok series in September 2023 that their wedding decision, which took place at Glastonbury in June of the same year, was primarily motivated by love as they had been together for ten years. However, it also stemmed from a place of past trauma and an urgent need to rebuild. Miley explained that the day she performed at Glastonbury, specifically June 30, 2019, marked the point when she realized that continuing the relationship was no longer sustainable for her life.

In the summer of 2019, finding myself newly single, I embarked on a romantic getaway to Italy with Kaitlynn Carter – Brody Jenner’s former partner. This journey served as an opportunity for us to unwind and enjoy each other’s company amidst the enchanting Italian landscapes.

All in all, Miley was associated with the ex-member of the Hills for just a few months, yet they continued to be friends even though they’ve never publicly discussed their often-documented period together.

By the end of 2019, Miley had connected with Cody Simpson and they dated for almost a year.

In an appearance on The Kyle and Jackie O Show in October 2019, the Australian singer expressed that they support each other in maintaining sobriety, which contributes to the strength of their bond. This aspect of their relationship is unique for him, as it’s the first time he’s experienced such mutual understanding. They are extremely aligned in their views.

In April, Cody shared with the Sydney Morning Herald that spending time with Miley is a wonderful aspect of his life. He finds her to be imaginative and motivating, fiercely autonomous, and someone who also inspires him to embrace his individuality.

Their romance fizzled in August 2020, but not because anyone came in with a wrecking ball.

Cody reminisced on his friendship with someone, saying that they transitioned from close friends to having mutual acquaintances, then spending time together for a period. He concluded that their relationship ended peacefully, it was just one of those stages in life, and he learned valuable lessons from the experience.

Miley couldn’t exactly take a blind date with Maxx Morando in the summer of 2021, but it turned out to be a blind encounter for her when a friend arranged their meeting.

“I thought, ‘The worst that can happen is I leave,’” she recalled to British Vogue in May 2023.

In November 2021, they were initially seen attending the Gucci “Love Parade” fashion event in Los Angeles. Since then, they’ve remained a couple.

Toward the end of 2024, Miley expressed to Harper’s Bazaar that he bears a strong resemblance to her. “In essence, we both have a light-hearted approach towards life,” she said.

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2025-05-10 18:18