From Kylie to Miley! A Look Back at Cody Simpson's Star-Studded Dating History

Can’t they just have a kiss and açai bowl in peace?! The Australian musician began to “Slide Away” from the friend zone with longtime pal Cyrus on Oct. 3, 2019, when the pair were spotted cozying up during a steamy “makeout session” over breakfast in West Hollywood.

Their whirlwind romance comes on the heels of Cyrus’ back-to-back splits with Liam Hemsworth and Kaitlynn Carter, and has prominently featured affectionate photos and videos of the new couple eating together, serenading each other and getting, uh, rather handsy.

Simpson confirmed on Oct. 12 that is was “safe to say” they’re official, adding, “I’m very happy. We are very, very happy. … We just have a ball, yeah, and that’s the most important part of a relationship, you know?”

While Simpson has dated other high-profile women, he said that his relationship with Cyrus is a “different experience” because of their longstanding friendship. “Any girlfriends I’ve had in the past has always been immediate romance,” he explained. “So it’s a different experience having been friends with somebody before and it developing naturally into something more.”

Simpson and the New York City-based model first went public with their romance in August 2018, when Wuestenberg posted a cuddly photo of the pair sailing together. They took a trip to Bali the next month and were photographed together a few more times before Wuestenberg seemingly spoke out about their split in January, sharing a photo of herself on Instagram with the cryptic caption, "All the Hollywood rumors are true."

She then delved into detail on her Instagram Story, sharing that her "boyfriend" — presumably Simpson, although she avoided naming names — broke up with her "in a really, really s— way" and that she'd "like to tell everybody about it, but I'm sure it would be not so good for his career, so I'll keep it quiet."

She spoke about feeling "abused emotionally" and shared a scathing poem about her former flame, referring to him as a "spoiled, privileged, self-obsessed, narcissistic conman," according to JustJaredJr.com.

The "Golden Thing" singer briefly dated Lindsay Lohan's younger sister Ali in 2018, living with her in an apartment that Lindsay claims to have furnished for them.

Lindsay seemingly threw some shade at Simpson (and his current girlfriend, Cyrus) in October 2019, after he won Australia's first season of The Masked Singer, on which she was a judge. "When you realise you failed. And you settle for less @codysimpson. Family is everything you won the masked singer but you lost on your future," she captioned a since-deleted photo of Simpson and her sister.

During the show's finale, Lindsay guessed that it was her sister's ex-flame behind the mask — and had a few choice words for him.

"If it is you, we have a lot to talk about, and this is not the arena for it," she said with a laugh. "I want my furniture back, because I bought your furniture for your house in Venice."

Simpson elaborated to Australian outlet Punkee on the backstory of Lohan's comment, explaining that he had been living in a "kind of beach shack" near Venice Beach, California, while he was seeing Ali "for a short period" and at the time he was "sleeping on a mattress on the floor because that was the vibe of the house."

Apparently Ali wasn't a fan of the vibe and said her sister was going to order a bed frame for the house, "but it never ended up coming and we didn't know where it went," Simpson told the outlet. Ultimately, Simpson said there's no bad blood between him and Lindsay, and that the they've even been texting since The Masked Singer ended.

While Simpson doesn’t yet seem to mind the spotlight in his new romance with Cyrus, he previously stated that being part of a high-profile relationship was what eventually prompted his split from Hadid in May 2015.

“I love my ex-girlfriend, I always will. It was an amicable, mutual decision, and we still talk every now and then, but the highly publicized thing made me uncomfortable,” the Free singer told DuJour after he and the model ended their on-and-off relationship of two years.

“Going out to dinner and there being all this paparazzi and stuff as soon as we split I had the realization that I was straying away from who I was as a whole person. I want to keep it low-key and focus on my music,” he added at the time.

While this photo now looks like a meme waiting to happen, at the time it was just a friendly run-in between Cyrus and then-pal Simpson, who was still dating Hadid. The trio were seen chatting at the 2015 Daily Front Row Fashion Media Awards, which came just one week after they all celebrated Simpson's 18th birthday together. For his party, Cyrus — who Simpson called "my chick" in a caption at the time — made the birthday boy two pizza cakes.

Cyrus may have only recently become Simpson's muse — inspiring his upcoming single "Golden Thing," which he serenaded her with while she was recovering from surgery for tonsillitis — but the pair have bonded over their love of music for years.

"A little johnny cash by the fire never hurt nobody," Simpson captioned a photo of their backyard jam session back in December 2014.

Simpson was rumored to be dating the youngest member of the Kardashian-Jenner family back in 2011, but neither he nor the makeup mogul publicly acknowledged the relationship at the time.

Years after they reportedly split, photos of the teens embracing surfaced in 2014, and Simpson finally spoke out about why he ultimately had a hard time Keeping Up with Kylie.

"The whole K-O-D-Y thing didn't really work out for me," he joked on E! about their short-lived romance.