Hailey Bieber’s Complete Dating History: From Justin Bieber, to Drake, to Shawn Mendes
Back in the days of yore before Justin Bieber was calling her “baby boo” and she was still using the last name Baldwin, Hailey Bieber was single and ready to mingle with pretty much exclusively hot celebrities. And it turns out she manifested several of them simply by tweeting a bunch, so it’s time to take a look back at Hailey’s dating history as inspiration.
Justin and Hailey were first spotted on a romantic dinner at Mr. Chow in New York back in 2015—but here’s the thing: She’d been tweeting about him for years. So, like, feel free to still keep DMing Paul Mescal, it just might work.
Anyway, things got serious enough for these two to go public on Instagram in photos that weren’t deleted during their breakup:
Speaking of the breakup, these two split in 2016 because Justin was allegedly jealous of Hailey’s “friendship” with Drake. A source told People that “Justin unfollowed Hailey on social media” and “wasn’t happy about [her friendship with Drake] and so they haven’t really been in touch in a bit.”
Drake: May 2016
Hailey and Drake were spotted having dinner in May 2016 after “hitting it off”at Drake’s Memorial Day party—and get this: He was later seen wearing her “h” necklace from said date night. Bold! Anyway, we visited the Library of Congress and found this incredible historic footage of the Memorial Day party in question, featuring the Snapchat dog filter (hello, old friend).
Jordan Clarkson: January 2017
Hailey and Jordan (who Hailey’s friend Kendall Jenner also dated) were linked briefly in 2017 when they were spotted together by TMZ, though honestly? They might have just been friends.
Cameron Dallas: June 2017
Dave Benett – Getty ImagesCameron and Hailey barely dated, but this lil’ tidbit about him meeting her parents was included in an Elle U.K. profile:
“During ELLE’s interview, YouTube megastar Cameron Dallas sits on a table behind with Baldwin’s parents—it was the first time they had met. ‘He’s not my boyfriend yet. Technically, I’m single’ she says, but the meet is making her jittery. ‘It makes me so nervous, oh my God. I don’t want my mom to be like, ‘So…’ she says, flicking her head between their table and where ELLE is sat.’”
Anyway, a source also told E! News that “Hailey wants to keep it low-key between them. It’s not serious, but they are definitely into each other.”
(Obviously, their “low-key” vibe didn’t last.)
Shawn Mendes: May 2018
Remember when Hailey and Shawn attended the Met Gala together? Yeah, turns out Hailey also manifested that:
Anyway, things between them didn’t last (one month after their Met Gala appearance, Hailey was dating Justin Bieber), but Shawn did tell Rolling Stone it was a more casual vibe anyway: “I don’t even wanna put a title on it. I think it was more of a zone of limbo.”
Justin Bieber: June 2018 – Literally Right Now
Justin and Hailey were spotted at a church conference in summer 2018, and a source told E! News they had two things in common: “They love to party and they love their church organization.” Cool! Anyway, before long they were making out in public places:
Got engaged in the Bahamas:
And then made their courthouse wedding official in September 2019:
They’ve been going strong ever since, though there’s been some slight drama thanks to Hailey’s dad Stephen Baldwin asking fans to pray for them as a couple. But Hailey shut the rumor mill down with a super cute post to Justin on his birthday, so!
