The rumored short-lived fling between Drake and Hailey Bieber

The “Peaches” singer seems happier than ever with Hailey. “I am now navigating the best season of my life” MARRIAGE!!” Justin wrote in an emotional 2019 Instagram post, adding that the experience of being married to Hailey taught him “patience, trust, commitment, kindness , humility and all that seems to be a good man”.

The drama resurfaced in early 2023 when Selenators speculated that Justin’s 29th birthday party favors were a hint at his ex. But on the bright side of things, it could have just been a nod to Justin’s love for his wife.

And, to be fair to Justin, he’s not the only one with a list of famous exes! Before marrying the Grammy winner, Hailey dated another singer: Shawn Mendes.

Though their time together was short-lived, the couple were seen holding hands on the Hollywood circuit, and Mendes was Hailey’s date to the 2018 Met Gala.

Mendes also documented his time with Hailey on social media, so at least they were serious enough to go Insta-official.

Less talked about is the fact that Hailey seems to have a thing for singers. Before Mendes, Hailey reached out to Drake, though they never confirmed a relationship.

Drake and Hailey Bieber went on a few dates in 2016

It’s unclear if Drake and Hailey Bieber officially dated before Hailey became a married woman.

People reported that they saw each other as a couple at her Memorial Day party in 2016, where they got “very affectionate” with each other.

A few weeks later, a source told the outlet that Drake and Hailey were “very casually dating, but he’s really into her. They met through mutual friends and are taking it easy.”

If by slow, the insider meant that Drake was wearing jewelry with Hailey’s initials while on a date with her, then sure. According to ET,, a witness noted that the model and the rapper seemed “in love” with each other as they drank and ate dinner. “They were totally absorbed in the conversation” and “very smiling [entre ellos]”,

However, just a month later, it seemed that the sparks had died down.

“I know [Drake] for a long time, I don’t know if people really know that,” Hailey told reporters at the awards. iHeart Radio Much Music Video Awards 2016, implying that she and the “God’s Plan” singer were just friends.

A source confirmed it, explaining: “[Drake y Hailey] they have always had a close friendship and a similar group of friends. They’re very playful with each other, but there’s nothing romantic right now.” The abrupt breakup could be because they were still getting over their exes, Rihanna and Justin Bieber.

Did Drake and Hailey Bieber have their exes in mind?

When Drake and Hailey Bieber got together in 2016, they had both just broken up. For Hailey, it was important that she take time to stay single after Justin Bieber broke up with her.

“I didn’t just jump into a relationship, I jumped into something else… I did other things to try to distract myself… but I didn’t look for someone to… come take the place [de Justin] ”, he reflected in “The Biebers on Watch”, which apparently implies that she was never in a relationship with Drake.

It’s unclear if it was a mutual decision to end things or the call was Hailey’s to end things.

But for Drake, there were additional complications in the form of Rihanna.

By his own admission, Drake had been in love with the “Umbrella” singer for a long time, so he might not be able to fully commit to Hailey.

And perhaps most tellingly, Hailey and Drake swooned right at the same time that Drake and Rihanna started to warm up. Coincidence? Maybe not.

“Drake has always wanted to make things work with Rihanna. They are still dating. Things get more serious when they are in the same place,” a source told People in July 2016.

Unfortunately for Drake, that ship crashed and burned. By 2018, the couple were no longer on speaking terms. Meanwhile, Hailey got the happy ending of hers and is still married to Justin, as of this writing.