Shawn Mendes' Romances With Camila Cabello, Hailey Bieber and Sabrina Carpenter

Shawn Mendes' love life's been all over the place ... but you can bet it's never been boring!

The "In My Blood" singer's racked up a bit of dating experience, and he's been linked to some of the most glowing faces -- we're talking natural beauty, folks, not just good skincare routines -- in all of Hollywood over the length of his career.

Here's a look back at how the singer's played the field over the past few years -- and how his career's entwined with one particular "Senorita."

Mendes initially encountered his eventual on-again-off-again girlfriend, Camila Cabello, while they were opening acts on Austin Mahone's 2014 tour -- how's that for a meet-cute?

While the two established a close friendship as they spent time together on the road, they didn't begin dating at first ... although they did release a collaborative track, "I Know What You Did Last Summer," in 2015.

Although Mendes and Cabello's friendship naturally set off rumors within their respective fanbases, they denied they'd been dating ... at least for a few years.

Mendes flat-out shot down the idea during a 2016 interview with People, where he claimed he and the "Havana" singer were never "a thing."

He did confirm, however, that Cabello was "one of those people who is just very easy to connect with" -- talk about foreshadowing!

Mendes didn't let the rumors about his supposed relationship with Cabello slow down his love life, as he ended up finding a connection ... with Hailey Bieber!

The singer and the influencer -- who was on a break from her relationship with her future husband, Justin Bieber, at the time -- were first spotted in each other's company at various events in late 2017.

The pair subsequently sent their fans into a frenzy when they accompanied each other to the Met Gala in 2018 and walked the red carpet together.

However, Mendes and Bieber's relationship appeared to fizzle out later that year, and she'd revived her romance with Justin by that November.

Mendes spoke about his fling with Hailey in an interview with Rolling Stone, and although he described the period of time as "a zone of limbo," he listed the influencer as one of the "coolest people ever."

Cabello remained present throughout Mendes' brief fling with Bieber, and the songwriters raised eyebrows when they released a track titled "Senorita," as well as a steamy music video for the song, in June 2019.

The singers were later spotted during various PDA-filled outings over the next few weeks, and they were pictured making out on several occasions.

A source then spoke to Entertainment Tonight and claimed while Mendes and Cabello had originally planned on chalking their romance up to a "summer fling," they wound up in a situation where they had "really fallen for one another."

The two went on to quarantine together during the early stages of the COVID-19 pandemic in Miami ... and they even adopted a dog named Tarzan during that period of time.

The fun and games came to a halt in November of 2021, however, when Mendes announced he and Cabello had separated, by sharing a post on his Instagram account.

While Mendes focused on his career for a few years, he was eventually linked to Sabrina Carpenter when they were spotted together in February 2023.

Although a source later told Entertainment Tonight the two were "seeing each other" and were doing their best to "keep things low-key" ... that March, their fling appeared to fizzle out in the subsequent weeks.

Mendes then briefly rekindled his romance with Cabello, as they began being seen in each other's company during various public outings.

However, their second try was short-lived, and a source told People in June the pair's "timing was wrong."