Miley Cyrus is one of the well-established singers in Hollywood. From her breakthrough role in Hannah Montana to her performing at the Grammys, the Flower singer flourished in her own ways.
As she celebrates her 33rd birthday, Cyrus has been in the eye of the world due to her music and her most talked-about relationships. Following her divorce from Liam Hemsworth, she has been like an open book. From dating one of the Jonas brothers to now, finally settled into her current stable, creative, and collaborative relationship with musician Maxx Morando, Miley Cyrus has come a long way.
1. Nick Jonas (2006–2007)
Miley Cyrus’s first highly publicized relationship was with her fellow Disney Channel star Nick Jonas. According to People, the couple dated from 2006 to 2007.
Their teenage romance, which fans famously nicknamed ‘Niley.’ Though it was initially kept secret, Cyrus later disclosed it in her autobiography and interviews. Their breakup was emotionally difficult for Cyrus, who later wrote about the same in one of her early hit songs, 7 Things.
2. Justin Gaston (2008–2009)
Miley dated model and country singer Justin Gaston for about nine months. She met him through her father, Billy Ray Cyrus, who had worked with Gaston on Nashville Star.
At the time of their relationship, Cyrus was 16 and Gaston was 20, which attracted media attention over their age difference. The relationship was relatively short-lived. The couple called it quits in 2009, just before the singer left to film The Last Song, where she met her future husband, Liam Hemsworth.
3. Patrick Schwarzenegger (2014–2015)
Miley Cyrus had a brief but high-profile relationship with Patrick Schwarzenegger, the son of Arnold Schwarzenegger and Maria Shriver. It lasted from late 2014 to early 2015.
The couple was frequently photographed together at events and USC football games. According to US Weekly, Schwarzenegger also admitted that Cyrus was his ‘childhood celebrity crush.’
The relationship faced some public challenges, including rumours of Patrick’s infidelity during a spring break trip, which he denied on social media. Ultimately, the pair split in April 2015, citing their conflicting life stages. He was in college at the time when she was fully focused on her career.
4. Stella Maxwell (2015)
In 2015, following her split from Patrick Schwarzenegger, Miley Cyrus had a fling with Victoria’s Secret model Stella Maxwell. The two were even photographed engaging in PDA, leading to widespread speculation about their relationship status.
As per Harper’s Bazaar, Cyrus addressed the attention by talking about her pansexuality and her general view on dating, stating she was going on dates but not into exclusively labeling every connection.
Maxwell, who is openly queer and sexually fluid, briefly dated the singer during this period. It marked Cyrus’s public exploration of dating women after her initial long-term relationship with Liam Hemsworth.
5. Liam Hemsworth (2009-2013; 2016-2019)
The relationship between Miley Cyrus and Liam Hemsworth began on the set of The Last Song in 2009 and was defined by its decade-long, on-again, off-again intensity.
They first became engaged in 2012, separated for several years, and then reconciled, eventually marrying in a private ceremony in late 2018. The couple repeatedly struggled to adjust to their different lifestyles and careers.
Their marriage lasted only seven months before they separated in August 2019, leading to their highly-publicized divorce. She later channeled her feelings about the divorce into her global hit Flowers.
Despite the drama, their connection remains the most significant and defining of Miley’s dating life due to its length and depth.
6. Cody Simpson (2019–2020)
Miley Cyrus and Australian singer Cody Simpson turned their longtime friendship into a romantic relationship. They started dating in late 2019.
Their romance was characterized by public attention and frequent social media scrutiny, including Simpson playing an instrument for her when she was hospitalized (via People).
The relationship lasted for about ten months, during which they lived together through the COVID-19 lockdowns. They split in August 2020, citing that they were at a fork in the road, with Simpson focusing on competitive swimming and Cyrus on her album Plastic Hearts and touring the world.
7. Maxx Morando (2021–Present)
Miley Cyrus has been in a serious and low-key relationship with musician Maxx Morando, the drummer for the band Liily, since late 2021. The relationship is more of a creative collaboration, with Morando co-producing several tracks, including Handstand and Violet Chemistry, on her successful 2023 album, Endless Summer Vacation.
Sources (via Teen Vogue) indicate their relationship is quite serious and good, with Morando’s private nature being seen as a positive influence on Cyrus after years of diverted romances. The couple has maintained a balance of public appearances and privacy, with the singer reportedly seeing a healthy, positive, and fruitful life with him.
Miley Cyrus’s journey through love, heartbreak, and newfound stability mirrors the evolution of her music and identity.
Which era of Miley’s love life do you think shaped her the most? Share your thoughts in the comments below!
