Hailey Baldwin Dating Timeline, Ex-Boyfriends, Relationship History

Hailey Baldwin may be a successful model with ties to companies like Ralph Lauren, Guess and UGG AND come from a super-famous celebrity family, but she didn’t become a must-know name until she became attached at the hip (not literally) to Justin Bieber. Fast forward a couple of years since their original hookup, and the 21-year-old and the “Baby” singer are ENGAGED!

Although the two are totally in love now, it’s not very surprising that Hailey also dated people who aren’t the Biebs. Before her engagement, she allegedly got with more than one 5 Seconds of Summer guy, some handsome rappers and athletes, too. And here they all are:

Luke Hemmings

Back in October 2015, Alec Baldwin‘s niece was reportedly hooking up with one of the hottest guys in 5SOS. The two were spotted on a “romantic dinner” in NYC, and rumors of a relationship began to spread like wildfire.

Once Hailey got wind of the speculation, though, she was quick to shut it down. “I never went on a date with Luke from 5 Seconds of Summer. So if everyone wants to chill, that’d be dope,” she tweeted. For reasons unknown, she deleted the tweet shortly after posting it.

Ashton Irwin

Despite reports that this other 5SOS boy was dating Halsey, Ashton Irwin was seen out and about with Hailey. The two grabbed a cup of coffee together, immediately igniting romance rumors. But onlookers said it didn’t look like there was any PDA, and Ashton told TMZ, “Hailey Baldwin is a very close friend of mine. She’s a wonderful woman. I’m not dating her.”

Chris Brown

TBH, we’re kind of hoping that this one isn’t true based on Chris’ history of violence towards women. Breezy apparently hooked up with the pretty model while both attended the Cannes Film Festival in 2015. The singer and Hailey had already hung out during a double-date in 2014 when Hails was still with Biebs the first time and the “Loyal” rapper was apparently dating Kendall Jenner.

If KJ & CB were for real, then that would be a major girl-code violation on Hailey’s part.


Happy birthday Kenny ??

A post shared by Hailey Baldwin (@haileybaldwin) on

Although they were spotted hanging out a bunch in 2016, People reported that the pair was “dating super casually.” Apparently, that was in part due to the model’s lingering feelings for her other Canadian love, JB! Speaking to E! News, Hailey said, “I’ve known [Drake] for about like four years. He’s a great friend.” While “friend’ doesn’t exactly suggest anything steamy, you never know the exact definition of the word when it comes to Hollywood relationships!

Lewis Hamilton

You know this cutie as the ex-boyfriend of The Pussycat Dolls singer Nicole Scherzinger, but it also looks like he dated this younger woman last winter. Around the same time that Hailey was non-exclusively dating Bieber, she showed up to the 2016 Elton John AIDS Foundation’s Oscar Viewing Party with Lewis and the two apparently looked “cozy” — but this race car driver had also been previously linked to Kendall! Hailey, what’s with that?

Jordan Clarkson

Hailey and Kendall are so tight, the Keeping Up With the Kardashians reality star actually designed a tattoo for her BFF. So, when it looked like Hailey was dating the same guy as Kendall, everyone was pretty much thinking, “WTF?”

Jordan and Hailey were spotted hanging in 2017, just before reports that KJ was actually dating A$AP Rocky came out, so it’s possible Kendall was totally okay with the duo exploring their relationship (as she was moving on to new peeps, too!).

Cameron Dallas

Hailey and fellow IMG model Cameron Dallas got super close in 2017, which led people to speculate that they were dating. An anonymous source told E! News, “It’s not serious, but they are definitely into each other.” But after several months of rumors, things ended when Hailey unfollowed Cameron on Instagram. Coincidentally, it was the same weekend she was at a Zoe Church conference in LA with her then-ex, Justin Bieber.

Shawn Mendes

When Hailey and Shawn Mendes showed up at the Met Gala this year, arm-in-arm, relationship rumors started flying. However, both of them claimed they were single. It seems like at least Hailey was telling the truth because she started seeing the Biebs again shortly after the event. But she did delete all the pictures of Shawn off her Instagram, which seems like a weird thing to do for someone who’s just a friend.

Justin Bieber

Hailey became one less lonely girl when Justin Bieber proposed /a> to her in the Bahamas on July 7. The couple had previously dated back in 2016 and reunited just a month before the engagement. Although they haven’t dated for very long, the two have known each other for years, so it’s no surprise that Justin chose to take the next step with one of his best friends!

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