Miley Cyrus: a romantic history 

It’s been a wild couple of months in Miley Cyrus’s world. In August, she ended things with Liam Hemsworth, who filed for divorce a few weeks later. At the same time the breakup was confirmed, she started dating Kaitlynn Carter, who had just split up from her husband Brody Jenner a week prior. In the last two weeks, Miley broke up with Carter, and a few days ago was seen kissing and cuddling Cody Simpson, a longtime of friend. 

So, what’s going to happen next? 

To make sense of it all, let’s go back into Miley’s History. 

The Handholding Period (2001 AD – 2003 AD)

In 2001, Miley first dated Tyler Posey after he appeared on her dad’s show, Doc. Yes, I know, perhaps we went a little too far back. But Miley was his first kiss which I think is super adorable! She was 7 and he was 9 at the time, so it was mostly cute handholding anyway. Tyler Posey’s glow-up was real though. I think he’s still dating Sophie Ali, but potential to revisit this?

The Golden Age (June 2006 AD – December 2007 AD)

Around June 2006, Miley started dating Nick Jonas, becoming the Disney Power Couple of the era. I remember it like it was yesterday. They toured together, wrote songs about each other, and the JoBros even appeared on Hannah Montana. It was bliss, until their December 2007 breakup. It was dramatic and shocked a lot of young hearts, including mine. But also closeted me saw that Nick Jonas was free now so it wasn’t too bad. 

The Post-Nick Phase (Early 2008 AD – Late 2009 AD)

Miley briefly dated Thomas Sturges. You might be wondering who Thomas Sturges is. Me too. They started dating at the beginning of 2008 because his mom wrote a song for Hannah Montana 2. By spring, they had broken up because a hacker had leaked “compromising pictures” of Miley and Thomas. It was mostly tame stuff of the two kissing on the couch and Miley in a bra (GASP), but Disney apparently pressured Miley to end the relationship.

Around the end of 2008, Miley started dating Justin Gaston, a contestant on her dad’s reality show Nashville Star. Miley was 15 and Justin was 20, so she’s basically dating a young Leo. Ew. She also refuses to confirm that she’s in a relationship on Ellen. The two broke up just before she left to shoot The Last Song, although rumours at the time suspected that her rekindled friendship with Nick Jonas was part of the problem.

The First Liam Era (August 2009 AD – September 2013 AD)

Finally. The good stuff. Liam and Miley met on the set of The Last Song. (Ironically, Justin Gaston is currently married to Melissa Ordway, who plays Liam’s ex-girlfriend in the movie. So Justin’s dated two of Liam’s exes.) By August, the two are locking lips in the Nashville airport. However, Miley still denies that they’re dating even in November of that year, claiming that Liam was her best friend.

Throughout all of this, they’re all coupley with each other on red carpets, in a Teen Vogue shoot, and at various events. But the seeds of discontent are sowed early for harvest. A year after the airport kiss, they suddenly break up. 

Back again in September.

Off again in November. 

Miley is rumoured to be with Josh Bowman, her costar on So Undercover in February 2011, though sources both confirm and deny the relationship.

By April 2011, Liam and Miley are pretty firmly back together, and rumours of their engagement start swirling around by early 2012. But Miley flat out denies it, until she doesn’t, confirming the engagement in June 2012.

The ring is super key by the way because while Miley talks about how happy she is, people start to speculate about a potential breakup by 2013 because she takes it off and on at various points in time. 
The engagement is off by September, after Miley twerks on Robin Thicke and a foam finger, an iconic moment for the books. Was that the reason they broke up though?

The Inter-Liam Period (September 2013 AD – January 2016 AD)

At the end of such a long and bumpy road, amidst rumours of grinding and cheating, it’s almost a relief at this point. Now Miley is free to do what she wants, including producer Mike WiLL Made-It, who she dates secretly for about nine months, and is pretty serious with according to Us Weekly. We later find out that the two started dating right after Liam and Miley broke up. He even meets her mom! But maybe it’s not that serious, because she’s rumoured to have kissed Kellan Lutz in December, which Lainey believed was more about famewhoreing than anything real. Also Avan Jogia and maybe even Jared Leto???? 

Miley also makes out with Britney Spears’s back up dancer. Cause why not? She also talks to Barbara Walters about the break-p, saying that she was “scared of ever being alone.” 

The Kennedy-Schwarzenegger Phase (November 2014 AD – April 2015 AD)

Is this Miley’s new long term relationship?

By November 2014, Miley’s with Patrick Schwarzenegger. He apparently was pining after her for years, though she denies it at first as rumours about the two swirl after being spotted together for Halloween. Patrick is Miley’s first real relationship post Liam, and the two are seen together at lots of events, including Art Basel in December. That’s also where people are sh-tting on Miley for corrupting Patrick with her devil’s lettuce smoking, wild twerking, provocative ways (2014 Lainey: as if he wasn’t familiar with all of this before Miley). 

It’s all good and fun until Spring Break hits, and Patrick is seen with a mystery girl wearing very little clothing. He posted three tweets insisting that the girl was just a friend but three tweets are a little bit overcompensating as an explanation non? They’re still together for a bit, but it’s pretty much over by the time April rolls around. Something about being at different places in life. She was focusing on her career, and he was focusing on mystery bikini girl (MBG).

The Rainbow Revolution (May 2015 AD – Fall 2015 AD)

In May, Miley reveals that she doesn’t consider herself heterosexual, that she doesn’t like labels and feels constricted by gender, and that she is attracted to both men and women, even admitting that she’s had relationships with both in the past. (Considering everyone up until this point has been male, we’re definitely missing people in this list.) 

Side Note: Miley also starts the Happy Hippie Foundation to support LGBTQ and homeless youth which is pretty f-cking cool of her.

Cut to June when people start to speculate that Miley is dating Stella Maxwell, rumours that pick up steam significantly after the pair are seen kissing in a parking lot in July (sups romantic). Allegedly, she was dating Stella just after she broke up with the Schwarz. Almost two months later, Miley comes out as pansexual on the cover of Elle UK, still insisting that she isn’t in a relationship despite lots of quality time, a kiss, and a W magazine photo shoot with Stella.

The two are never confirmed together, and there are even rumours that Miley hooks up with Dane Cook. Ew.

The Second Liam Era (January 2016 AD – August 2019 AD)

By October of 2015, Miley is borrowing Liam’s costume for Halloween and in November is helping him to adopt a dog. Apparently, they had a secret friendship while they were apart. Social media posts surface of Miley in Australia for the New Year, hanging out with friends of the Hemsworth clan, and even Liam himself. And OMG THE RING. IS. BACK. Are they engaged?

Yes. PEOPLE confirms in January, and everyone is happy about it, especially Miley who packs the moving truck and heads on over to Liam’s place. Naturally, Liam is the saint who was just giving Miley space to figure herself out. And Miley is Liam’s “Little Angel”, which is kind of cute but also a little gross and patronizing, especially the number of times he uses it. (Is that why her new song is called “Don’t Call Me Angel?”)

Most of 2016 and 2017 is filled with outings, matching tattoos, cute car duets, social media posts, Little Angel (ugh) shout outs, birthdays, holidays, and even a pregnancy scare (it’s a tofurkey!). She only confirms the engagement with Ellen in October 2016 (Miley only announces things on Ellen), and a year later, releases her album Younger Now with songs about Liam and Stella on it.

Everyone is super into this, and the cute carpets and stories in 2018. Which is probably why we all screamed for a brief moment when Miley deletes her Instagram photos in July, but everything’s okay. At least with Miley and Liam.

The Great Malibu Fire (November 2018 AD)

In November, a horrific fire destroys several homes in Malibu, including Miley’s and Liam’s. It’s a tense and emotional time, but the two are safe, along with their entire zoo of pets, all of whom are rescued by Liam. Miley f-cks his brains out as a thank you. But as Lainey wrote earlier this year:

“When decisions are made in that frame of mind, they’re often spontaneous and desperate. Of course they’d feel desperate, desperate to hold on to anything solid, desperate to protect what they love, desperate to wrap themselves in each other, in whatever life that remained, because in that disaster, they lost so much.”

Miley and Liam are secretly married in December, and we find out through other people’s Insta Stories. And things are pretty good for a while, though in July, Miley admits to Elle that she really doesn’t fit the traditional wife role, and doesn’t even like the word. (Correction: Miley only announces things on Elle(n)).

By August 10th, she’s NOT WEARING THE RING, and PEOPLE confirms that she and Liam have split that evening. Which comes right before images of her and Kaitlynn Carter (who she’s on a trip with in Como, Italy) kissing on a warm, sandy beach. 

The ensuing fallout gets pretty nasty. There are some initial nice sentiments, but pretty quickly Team Miley and Team Liam are throwing blame, people are sh-tting on Miley again for her can’t-be-tamed ways, and there’s back and forth gossip about how it all went down, including whether Liam even knew about the split before the announcement, or Miley tried to get the two into therapy earlier on.

"Slide Away" (AKA Wrecking Ball 2) is released and now we’re wondering if it was the Whiskey and Pills that caused the split. Liam files for divorce. Miley gets custody of the pet zoo. It seems pretty definitively over. Right?

The Summer of Kaitlynn (August 2019 AD – September 2019 AD)

Like all great histories, this one started with a catastrophe. But as the dust settled, Miley and Kaitlynn keep dating for a bit, continuing their Italy tour with Miley’s sister. Kaitlynn gives Miley support for her VMA performance of Slide Away (her dad’s at the event too). There’s brunch with mom, a lot of matching outfits, and even rumours of moving in together. We’re all wondering whether this is going to be a long term relationship, or whether Miley is just enjoying a summer fling.

The Modern Era (September 2019 AD – Present)

Definitely the latter, cause Miley and Kaitlynn break up near the end of September, although they’re still friends. Things might have been moving a little too fast, too soon. Or maybe Miley just wants to be single now.

Which is why she was spotted kissing Cody Simpson on Thursday in an LA Grocery Store (also romantic), and again on Friday at a Backyard Bowls. Cody and Miley go way back and were even rumoured to be dating for a while during the Inter-Liam Period. And he had a big crush on her back when he was 15. 

The Takeaway
Putting it all together like this, there are a few patterns that you can see in the way Miley dates. She doesn’t like labels, especially ones that constrain her into gendered boxes. She also doesn’t like to confirm that she’s dating people until much later in a relationship. That might come from the label hating thing, but that also might be her perspective on how she dates. Everything is fluid and experimental until it’s not. She’s single until she’s not.

But Miley also likes to date, and though she often talks about how she’s ready to enjoy the single life, she never really does, especially after a long term relationship ends. On Friday, Miley posted her frustrations on Twitter. 

There are some important points here. First, there is definitely a double standard to the way we perceive how men and women act after a breakup. I’m all here for Miley dating whoever she wants, however long she wants, whenever she wants. Let’s find whatever 2019’s equivalent of a Britney Spears backup dancer is. 

Second, Miley is also aware of how we’ve been watching her grow as a child and a teen. She’s only now experiencing dating as an adult. Dating when you’re younger is confusing and weird, and it’s even weirder when the world is watching your every move. I’ve asked myself why I’m so invested and interested in Miley’s dating life. I think it’s because as she navigates the treacherous dating world, we learn more about Miley herself. Like when she was dating Stella Maxwell, we learned that she was pansexual. For me, following Miley’s relationships helps me learn more about myself. How I want to date and who I want to date. (Australians with abs.)

The new theme is that Miley’s “grown now.” It’s in the tweet, it’s a lyric in "Slide Away", and it’s the messaging that we’ve been getting from her on social media. And maybe that’s why it didn’t work out with Liam, because they’ve changed so much since they first got together. But I’m curious to see what Grown Miley dates like. Will see explore the single life and focus on herself? Is Cody Simpson going to stick around for long? If this were Young Miley, I’d say no. But with Grown Miley, I’m no longer sure.