If you’ve been following pop culture long enough, you know the internet has a memory like an elephant. Back in 2016, the world was a very different place. Justin Bieber and Hailey Baldwin were "just friends" (mostly), and Drake was busy dropping Views. But for a few chaotic weeks in May and June of that year, the tabloids shifted focus to a pairing nobody saw coming.
Hailey Baldwin and Drake. It wasn't just a random rumor started by a bored blogger. We’re talking about late-night dinners, PDA-filled house parties, and one very specific piece of jewelry that had the "Jelena" stans in a total tailspin. Honestly, it’s one of those weird celebrity blips that feels like a fever dream now that Hailey is officially Mrs. Bieber and a mom.
The Memorial Day Party That Started It All
It basically all kicked off at Drake’s Hidden Hills mansion during his infamous Memorial Day bash in 2016. You might remember the Snapchat clips. People were everywhere, the music was loud, and according to multiple onlookers at the time, Drake and Hailey were "getting cozy."
They weren't just standing in the same VIP section. A source told People magazine they were "very affectionate" throughout the night. It wasn't just a quick hello. They spent a huge chunk of the party together, laughing and acting like a pair that was definitely more than "just acquaintances."
Wait, it gets better.
The very next night, they were spotted at Ysabel in Los Angeles for what looked like a textbook date. They sat in a private area, totally engrossed in conversation. After dinner, they headed over to The Nice Guy—because apparently, you can't be a celebrity in 2016 without going there—and they eventually left together.
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The Case of the "H" Pendant
This is where things got really suspicious. If you look at the paparazzi shots from that week, Drake was seen wearing a thin gold chain with a gothic-style "H" pendant.
Does that sound familiar?
It should. It was Hailey’s. She had been seen wearing that exact same Jennifer Fisher necklace for weeks prior. Seeing a 29-year-old Drake rocking a 19-year-old model's initial necklace is... well, it’s a choice. In the world of celebrity signaling, that’s basically the equivalent of changing your Facebook status to "In a Relationship."
The necklace swapping lasted for a bit, and it fueled the fire that this wasn't just a one-night thing. They were seen together again in June, sparking headlines that Drake was "moving on" from his long-standing flirtation with Rihanna.
Was Justin Bieber Jealous?
You bet he was.
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At the time, Justin and Hailey were in one of those "it's complicated" phases. They had traveled to Anguilla together earlier that year, but they weren't exclusive. However, sources close to the Biebs claimed he wasn't thrilled about Drake—who he considered a "big brother" figure—taking Hailey out on the town.
Hollywood Life (take them with a grain of salt, but the sentiment fits) reported that Justin even warned Hailey that Drake was a "player." Whether that was a genuine brotherly warning or pure jealousy is up for debate. But it’s worth noting that Justin actually unfollowed Hailey on Instagram around this time.
That’s 2016 for "I’m mad at you."
The Aftermath: Just a Summer Fling?
By the time July rolled around, the Hailey Baldwin Drake rumors started to fizzle out.
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Drake went back to being linked with Rihanna (and eventually Jennifer Lopez), and Hailey continued her path toward eventually reconciling with Justin for good. When asked about it later, the party line was always "just friends."
Hailey has a history of keeping her circle tight with A-listers. She’s been linked to Shawn Mendes, she’s best friends with the Jenners, and she knows everyone in the industry. Looking back, it’s highly likely that she and Drake were just having a fun, flirtatious summer moment while she was trying to figure out her messy situation with Justin.
What We Can Learn From the Hailey-Drake Rumors
If you're looking for deeper meaning in celebrity gossip, this era is a masterclass in how Hollywood handles "rebound" energy.
- Social media is the new diary. Those Snapchat filters and Instagram unfollows told a whole story before a single rep could release a statement.
- Jewelry matters. In the celebrity world, a borrowed necklace is a public declaration.
- Friendships are fluid. Despite the awkwardness, Drake and Justin remained on decent terms, eventually collaborating again.
If you're ever feeling nostalgic for the mid-2010s, just remember the time Drake wore an "H" necklace and the entire internet thought the world was ending. It’s a reminder that even the biggest stars have those weird "what was I thinking?" phases in their dating history.
For those curious about how Hailey moved from these rumors to her current life, the best thing to do is look at the timeline of her 2018 reconciliation with Justin. It shows how much she grew from those "Nice Guy" dinner dates to building a family.