While Shawn Mendes opened up about his sexuality while performing at a concert on Monday, he has been a little more private about his dating life over the years.

During a show at Morrison, Colorado’s Red Rocks Amphitheatre this week, the singer-songwriter, 26, spoke to the crowd about his early start in the music industry and .

“I was really young when I started. I was 15 years old,” he said in his address, footage of which has been . “The truth is that I didn’t get to do a lot of 15-year-old things and discover parts of myself that you do at 15.”

“There’s this thing about my sexuality, and people have been talking about it so long,” he went on, adding that it was “kind of silly, because I think sexuality is such a beautifully complex thing, and it’s so hard to just put into boxes.”

“It always felt like such an intrusion on something very personal to me. Something that I was figuring out in myself, something that I had yet to discover and still have yet to discover it,” he continued.

“The real truth about my life and my sexuality is that, man, I’m just figuring it out like everyone. And it feels really scary because we live in a society that has a lot to say about that. And I’m trying to be really brave and just allow myself to be a human and feel things. And that’s all I really want to say about that for now.”

He then spoke about his unreleased track “The Mountain,” which includes the lyrics: “You can say I’m too young/ You can say I’m too old/ You can say I like girls or boys, whatever fits your mold.”

“Writing the song felt really important to me because it felt like a moment where I could address it in a way that felt close to my heart,” he explained. “And I guess I’m just speaking freely now, because I just want to be able to be closer to everyone and just kind of be in my truth.”

While Mendes’ current dating status is publicly unknown, the star has made headlines over the years with his previous relationships.

Hailey Baldwin Bieber

Mendes’ relationship with the then Hailey Baldwin made headlines in late 2017, when reports emerged that the two were seen holding hands while attending a star-studded Halloween party.

Weeks later, the two were photographed hugging one another in Mendes’ native Canada as they walked through the streets of Toronto. At the time, she had broken up with pop singer several months earlier.

As a sign of the times, their romance was seen as all but official when Mendes shared a photo of the two together on his account in April 2018.

Sending the chatter into overdrive one month later, the two walked the red carpet together at the hot-ticket Met Gala in May 2018.

While it was seen as the big confirmation of their romance, Mendes People that he and the model were “friends.”

“No, we were not making our big debut,” Mendes said as they attended the Met Gala. “We were both asked to walk by Tommy Hilfiger.”

“Obviously Hailey and I are friends, and it was just really cool for me to be able to walk with her because she’s a vet and it was my first year, so it kind of took the pressure off a little bit,” he added. “I was thrilled to be able to go with her.”

Mendes finally confirmed their relationship in an interview with Rolling Stone in November 2018, after the pair had gone their separate ways.

“I don’t even wanna put a title on it,” he told the publication of their relationship. “I think it was more of a zone of limbo.”

The musician also addressed the fact that Baldwin Bieber got engaged to her now-husband Justin Bieber just one month after she attended the Met Gala with him.

“I texted Hailey, ‘Congratulations,’ and I really am happy for them,” Mendes said. “She’s still one of the f****** coolest people ever—she’s not just a beautiful person visually, but she’s one of the most beautiful hearts I’ve ever met.”

He added: “I think I’m an idiot to not, you know… But you can’t control your heart.”

Camila Cabello

Work first brought Camila Cabello into Mendes’ orbit in 2014, when the two opened for Austin Mahone. However, it took several years for romance to blossom.

The musicians, who have two hit songs together—”I Know What You Did Last Summer” and “Señorita”—were friends for years, but they began dating in 2019. They confirmed their relationship later that year, following months of speculation.

Showing that things were going from strength to strength, the stars adopted a puppy, named “Tarzan,” together in November 2020. However, exactly one year later, the two announced that they had gone their separate ways.

The celebrity couple in November of 2021 via Instagram Story posts. “We’ve decided to end our romantic relationship,” the statement read. “Our love for one another as humans is stronger than ever. We started our relationship as best friends and will continue to be best friends. We so appreciate your support from the beginning and moving forward.”

In a video post shared on Instagram back in March 2022, Mendes discussed what happens in the aftermath of a breakup.

“Oh f***, you don’t realize when you break up with someone you think it’s the right thing, like, you don’t realize all the s*** that comes after it,” he wrote. “Who do I call when I’m in a panic attack? Who do I call when I’m on the edge? That’s the reality that kind of hit me. Like, ‘Oh, I’m on my own now’ and I hate that. That’s my reality you know?”

Around the same time, Cabello also spoke out about the breakup in an interview with Zane Lowe. She explained that her priorities had changed. “My focus was just, how can I live a happy life and be in a healthy, happy relationship? I was doing therapy a lot. My focus really has shifted.”

The “Havana” singer added: “And even now while I’m in promo mode, honestly, if I’m not having fun, what’s the f****** point? I think as I get older, yeah, the priorities shift. We both started so young too, we’re really learning how to be healthy adults. And that sometimes means not having your number one focus be your career. And that’s okay.”

Speculation they had rekindled their romance was sparked in April 2023, when video footage emerged of the musicians at the Coachella Festival in the Californian desert. This speculation spilled over into the following month, when they attended ‘s Eras Tour during a stop in New Jersey.

Sabrina Carpenter

The nature of Mendes’ relationship with Sabrina Carpenter was always officially labeled as a friendship—but that did little to quell speculation.

The singers were first photographed strolling through the streets of Los Angeles together in late February 2023. They were also seen departing ‘ album release party for Endless Summer Vacation together several days later.

Quoting an unnamed source, Entertainment Tonight reported that the two were in a romantic relationship while “trying to keep things low-key.”

However, Mendes insisted that this was not the case when he made an appearance on Dutch TV show RTL Boulevard in March 2023.

“We are not dating,” he said of his relationship with Carpenter, before turning attention to reason for his promotional appearance. “I think we should talk about Tommy Hilfiger probably more than Sabrina. But thank you.”