Cody Simpson Gets Honest About His Past Hollywood Romances

Cody Simpson is reflecting on some of the most talked-about relationships from his early years in the spotlight.

During a recent podcast appearance, the Australian singer looked back at romances with several famous women, including Kylie Jenner, Gigi Hadid, and Miley Cyrus.

As he revisited those moments, Simpson offered candid memories about how those connections shaped him.

Cody Simpson Opens Up About Dating Kylie Jenner

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Cody Simpson revealed that Kylie Jenner was actually his first girlfriend, recalling how the two met when they were both teenagers navigating early fame.

Speaking on the “We Need To Talk with Paul C. Brunson” podcast, Simpson explained that their relationship began after a chance encounter at a movie premiere.

The pair crossed paths in 2010 at the Los Angeles premiere of “The Twilight Saga: Eclipse,” where Kylie and her sister Kendall Jenner were interviewing guests on the red carpet. Simpson said the meeting led to them exchanging numbers and eventually spending time together.

Reflecting on their short-lived relationship, he said, per PEOPLE, “It was young. I took her to the movies or something, and we dated for about a year, and I think we just bonded through being in these unique situations.”

Simpson added that their shared experiences in the spotlight helped them connect.

He said, “So it was nice. I think it’s just nice to relate to somebody at that age in that world.”

Simpson Reflects On ‘First Love’ Gigi Hadid

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When the conversation turned to Gigi Hadid, Cody Simpson described the supermodel as someone who made a lasting impression on him.

He explained that he first noticed Hadid when he saw her in an advertisement. According to Simpson, the moment stuck with him immediately.

The singer said he spotted her “first billboard for Guess” at a shopping mall and remembered thinking she was “the hot older girl.”

Eventually, a mutual connection helped bring them together. A friend gave Simpson Hadid’s phone number, and he decided to take a bold approach to starting a conversation.

“There was no music video. No plans for a video, the videos have all been shot, and this was like right around, I was doing my second album,” Simpson recalled about his initial phone call.

He continued explaining the unusual tactic he used to break the ice. He shared, “I’m pretty sure I pitched her this whole concept that didn’t exist, and she goes, ‘Yeah, okay.’ And I think that just broke the ice.”

After that, he admitted he quickly shifted the conversation, saying, “So I started texting her and I’m like, ‘Ah I don’t think the video is going to happen anymore, but like, do you want to catch up? Do you want to go out for food or whatever?’ ”

Cody Simpson Recalls Dating Gigi Hadid

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Their relationship soon developed into something deeper. Simpson fondly recalled their early dates and the excitement he felt at the time.

“And I just got in my first car, and I’m feeling like the man, you know,” he said. “And I couldn’t even legally drive by myself at the time, but I think I went, picked her up, and we hung out.”

The singer described their connection as meaningful and memorable. “It was kind of like she was my first love, man. Absolutely,” he shared.

Simpson said their relationship lasted roughly two years, though it had its ups and downs. During that time, Hadid even joined him while he was on tour.

“We were together for, on and off, about two years, but we started hanging out and a couple weeks later, she came on tour with me,” he said.

He also recalled becoming familiar with Hadid’s well-connected family during their relationship.

“Her stepdad at the time was David Foster, an incredible music producer, who at the time I don’t think I appreciated enough, having that relationship with him,” Simpson explained, adding that Foster sometimes joined him in the studio.

Looking back, Simpson believes the relationship came into his life for a reason. “The universe brings people together when they’re supposed to be together … We were supposed to be together when we were and learnt stuff from each other,” he noted.

Simpson Talks About His Relationship With Miley Cyrus

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Cody Simpson also reflected on his romance with Miley Cyrus, which developed years after his relationship with Hadid.

The two artists first became friends long before they dated. According to Simpson, their early bond formed when they were both navigating the pressures of growing up in the public eye.

“We did all Covid lockdown and everything together. But we met back when I was 18,” Simpson explained.

He remembered how their friendship grew through shared experiences, noting, “We used to go and party together and hang out, and we just always had a lot in common, and she did one of my album artworks for my song. It was called Flower.”

Simpson also spoke about Cyrus’ journey away from her early pop image and how their lives intersected during a period of change for both of them.

“She obviously rebelled very publicly from that over the years and went through certain things,” he said. “And I think when I started to go through that, she came into my life, and helped me navigate it in some ways.”

As Simpson’s career direction shifted, their friendship deepened again.

“When I went independent and started doing a more singer-songwriter thing, I was a downright hippie for a couple of years, and she was just like my friend during that period,” he explained.

The pair eventually reconnected after losing touch for a while.

He said, “And then we lost touch for a few years. And then, when we were a little bit older, and I guess more mature, we started talking again, and at that time it turned into something else.”

Simpson said he still looks back on that chapter of his life with appreciation.

He shared, “And again, it’s one of those things. It was very much, we were very much meant to be together at that time, we were both sober and in very different places to what, you know, we were when we were friends back in the day. We were kind of exploring what we’d both just been through … I’ll always be grateful for that.”

Life After Cody Simpson’s Famous Relationships

While Simpson’s past romances often captured headlines, his life has continued to evolve in recent years.

The singer has also dated Ali Lohan, the sister of actress Lindsay Lohan, as well as model Clair Wuestenberg.

More recently, Simpson was in a long-term relationship with Australian Olympic swimmer Emma McKeon. However, the pair reportedly ended their relationship in late 2025 after four years together.

According to Simpson’s sister, podcaster Alli Simpson, the two athletes have since gone their separate ways. She revealed during an appearance on Australia’s “The Morning Show” that her brother and McKeon have “moved on.”

Simpson has since been linked to U.S. influencer Adelia Clark after the pair were photographed together in Los Angeles, suggesting the singer may be entering yet another chapter in his personal life.