Hailey Baldwin's Boyfriends (Left to Right) Justin Bieber. Credits: Kevork Djansezian / Stringer / Getty Images, Hailey Baldwin. Credits:Nicholas Hunt / Staff / Getty Images, Shawn Mendes. Credits:Jason Merritt / Staff / Getty Images and Drake. Credits:Justin Sullivan / Staff / Getty Images

As with most millennial celebrities today, their lives are heavily publicized on social media. Most of them will share details about their personal lives, and fans are always hungry for the latest gossip. Recently, fans have been extra interested in Hailey Baldwin’s dating history, especially after she was recently proposed to by one of the biggest pop stars on the planet! Who are we talking about? Hailey Balwin and Justin Bieber! But who was Hailey Baldwin dating before The Biebs popped the big question? Keep on reading for all you need to know about the list of former Hailey Baldwin boyfriends.

Hailey Baldwin Dating Timeline

Hailey Baldwin. Credits: Nicholas Hunt / Staff / Getty Images (Left to Right) Luke Hemmings. Credits:Kevin Winter/ Staff/ Getty, Justin Bieber. Credits:Kevork Djansezian / Stringer / Getty Images Getty, Lewis Hamilton. Credits:Mark Thompson / Staff / Getty Images, Drake. Credits:Justin Sullivan / Staff / Getty Images, Cameron Dallas. Credits:Mike Marsland / Stringer/ Getty Images, Shawn Mendes. Credits:Jason Merritt / Staff / Getty Images, Justin Bieber. Credits:Kevin Winter / Staff / Getty Images

Recently, Hailey Baldwin has made headlines for her sudden engagement to one of the world’s biggest stars, many are taking a look back at the romances she once had in her life—and rumored ones, too! Just prior to her recent re-developed relationship with Justin Bieber, there was another certain Canadian boy on her arm—Shawn Mendes! However, it was never clear if there were actually romantically dating or not. It’s also why the sudden engagement to Bieber comes as such a shock! (Haven’t the two been back together for like five minutes?!) But Hailey is gushing about another “incredible person” in her recent tweet.

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Nonetheless, Baldwin seems to have a thing for Canadian men. So, without further ado, here’s her boyfriends list!

Hailey Baldwin’s Dating Timeline:

  • Justin Bieber (June 2018-present; engaged)
  • Shawn Mendes (2017 – June 2018; rumored)
  • Cameron Dallas (2016 – 2017)
  • Drake (2016)
  • Lewis Hamilton (2016; rumored)
  • Justin Bieber (2015 – 2016)
  • Luke Hemmings (2015; rumored)

Justin Bieber, Again

Timeline: June 2018 – Present (Engaged)

Fast forward to 2018, and Jailey were seemingly back on! The couple was spotted back together in recent weeks, looking more in love than ever before! Now, girls everywhere are crying at the fact that Bieber has finally locked himself a woman!

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It was reported that Bieber proposed to Baldwin while the two were vacationing in the Bahamas over the weekend, though neither of them have commented yet on the news.

A source exclusively told E! News, “They are engaged. It happened while on vacation at Baker’s Bay. They flew in from New York on the 6th and have been having the time of their lives. Justin is happier than ever and wants to be with Hailey. His family is very supportive and know he has been at his best lately. Everyone is very happy for him.”

Apparently, his family is so happy for him they too couldn’t even contain their online excitement! Bieber’s dad Jeremy took to Instagram to post a cryptic message saying how “proud” he is for the next chapter of his son’s life. And in a tweet on Saturday from Hailey’s dad, Stephen Baldwin (which has since been deleted), he wrote that God is “moving the hearts of JB & HB” and hashtagged it with “#thebestisyettocome” while also tagging Bieber’s parents to congratulate them, as well.

But we needed more confirmation from the sources themselves.

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As if they heard the prayers of millions of Beliebers, Justin Bieber and Hailey Baldwin took their own social media accounts to confirm they are indeed happily engaged to each other.

Shawn Mendes

Timeline: 2017 – June 2018 (Rumored)

In May 2018, Shawn Mendes and Hailey Baldwin were the talk of the town at the MET Gala when they appeared together on the red carpet looking like literal heaven. But neither of them ever confirmed a romantic relationship! Even when Mendes talked about his time at the Gala with Baldwin, he himself said, “We’re really good friends.”

Fans were shocked to hear the news, as the couple looked so adorable at the event together! (Most were hoping it was finally their big debut as a couple!)

Several photographs captured at the event show the pair smiling and laughing as they looked into each other’s eyes, arm in arm, and you could seemingly cut the chemistry with a knife! At one point, Mendes even bent over to fix her dress trail for the paparazzi! (It was an adorable “boyfriend” thing to do!)

“It’s funny, she’s such a pro with this type of stuff,” he said about her time at the Gala. “I want it to be amazing for her, so I’ve been trying the past 24 hours to be really silly so that she stays on. I’m happy to walk with her–she’s amazing.”

But fans were not so convinced about the whole “just friends” thing and were shipping them hard!

Baldwin also commented on the rumors saying, “He’s a friend of mine and we hang out, so I see why people obviously want to make assumptions.”

She added that everyone always jumps to conclusions every time she is seen hanging out with a guy and said, “But I don’t ever really feel like I have to explain myself. It’s kind of my business and the other person’s business. That’s it.”

The pair met on Twitter in 2013 when Baldwin tweeted, “Hey Shawn Mendes, let’s date so you can sing to me all day.”

The tweet has since been deleted, but the rumors continued.

But sources said they’ve gone on private vacations together to Europe and some reports even said they were spotted kissing at Rita Ora’s MTV EMA Awards after-party in London! So, why were they never exclusively dating? Did Shawn get friendzoned?

That’s the question everyone is asking.

Cameron Dallas, IMG Models Unite

Timeline: 2016 – 2017

Entertainment news sites confirmed that Baldwin was in a casual dating relationship with fellow IMG model, Cameron Dallas in 2016-2017. They met through friends and instantly clicked as they had the same social circle, which made their relationship natural and practically inevitable.

Dallas and Baldwin attended the 2017 Met Gala together. And although they didn’t want anything serious, they enjoyed spending time together.

Dizzy for Drizzy

Timeline: 2016

Canada’s hottest rap artist Drake also made the Baldwin dating timeline list. They were spotted hanging out a lot during the summer of 2016.

Sources claimed that they were casually dating. But perhaps this was because Baldwin was still reeling from her feelings for another certain Canadian artist…

In an interview, Baldwin said she’d known Drake for about four years adding, “He’s a great friend.”

Friend-zoned again?!

When it comes to Hollywood relationships, you can never tell for sure! (Or is that just when it comes to Hailey Baldwin’s love life?)

It’s Hamilton Time

Timeline: 2016 (Rumored)

Lewis Hamilton, race car driver and The Pussy Cat Dolls’ Nicole Scherzinger’s ex-boyfriend, was also seen hanging out with Baldwin in 2016. Their sightings occurred around the same time she was “non-exclusively” dating Justin Bieber (the first time around).

The pair showed up to the 2016 Elton John AIDS Foundation’s Oscar Viewing Party and seemed intimate.

But rumors of their relationship fizzled out as quickly as they stopped hanging out.

High-Profile Bieber Love

Timeline: 2015—2016

The model’s highest-profile Hollywood romance was with Canadian pop sensation, Justin Bieber in 2016. (Again with the Canadian boys!) Bieber was open about their relationship, posting hot photos of the couple on the ‘gram, and told a magazine, “[Hailey] is someone I really love.”

Despite the public appearances, Baldwin had something different to say about things and stated, “We are not an exclusive couple. He’s about to go on tour.” Regardless, the two seemed to fall for each hard and fast, possibly causing both of them to pump the brakes and figure things out. According to sources, their split was especially hard on both of them.

“We didn’t speak for quite some time and there was a lot of weirdness that went on,” said Baldwin following their split. “But it brought both of us to the realization that we just work much better as friends. He’s somebody I really cherish. Now it’s a very mature situation. It’s good.”

Bieber also felt the same and had a tough time when they decided to part ways in 2016. He told GQ Magazine that he didn’t want to rush things with Hailey in case she truly ended up being “the one.”

He told the magazine in February 2016, “What if Hailey ends up being the girl I’m gonna marry, right? If I rush into anything, if I damage her, then it’s always gonna be damaged,” he said. “It’s really hard to fix wounds like that. It’s so hard … I just don’t want to hurt her.”

Apparently, the publicity surrounding their relationship really took a toll on Baldwin, too. She said she didn’t want attention just for dating somebody.

“It’s hard to date somebody in this industry. You have to have really thick skin and be very strong. You have to focus on the person and nothing else,” she explained after their breakup.

A Quick Shut Down for Luke Hemmings

Timeline: 2015 (Rumored)

Fans speculated that Baldwin was in a relationship with 5 Seconds of Summer’s lead vocalist and rhythm guitarist, Luke Hemmings after they were allegedly seen together having dinner in New York City.

Baldwin quickly shut the rumors down by tweeting, “I never went on a date with Luke from 5 Seconds of Summer. So, if everyone wants to chill, that’d be dope.”

However, shortly after posting the tweet, she deleted it.

Chris Brown?

Timeline: 2015 (Rumored)

Rumors circulated in 2015 that Baldwin got involved with Rihanna’s ex-boyfriend, Chris Brown.

The hip-hop artist and Baldwin both attended the Cannes Film Festival that year. But they had reportedly already met and hung out during a 2014 double-date when she was dating Bieber, and Brown was allegedly seeing Kendall Jenner. Again, this one may have just been smoke and mirrors…

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