Justin Bieber and Hailey Baldwin's Road to Engagement

  • July 8, 2018
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Justin Bieber and Hailey Baldwin‘s road to engagement began more than three years ago.

The two have known each other since they were teens but sparked romance rumors in late 2014. They dated on and off and were even rumored to be engaged in 2015, following a bogus news report.

Their romance sizzled over the 2016 New Year’s holiday, when they vacationed in the Caribbean. Weeks later, they spent Super Bowl 50 Weekend together.

During the next two years, the two spent time apart dating other people; Last fall, Justin rekindled his relationship with Selena Gomez for a while, while Hailey and Shawn Mendes sparked romance rumors.

Justin and Hailey reignited their own flame last month, and have since traveled together to places like Miami and New York City, where he proposed to her this weekend.

Hailey Baldwin, Kylie Jenner, Kendall Jenner, Justin Bieber


Hailey celebrates her 18th birthday with Justin and other friends, such as Kylie Jenner and Kendall Jenner. No romance rumors yet.

Hailey Baldwin, Justin Bieber, Instagram


Hailey and Justin appear together in Instagram pics, sparking romance rumors.

“I’ve known him since I was so young‚ÄĒsince I was like 13‚ÄĒand we’ve just been good friends over the years,” Hailey tells E! News¬†at the time. “We have just stayed close and there’s nothing more to it than that.”

Justin Bieber, Instagram


“People are crazy. I’m super single and this is my good friend u would know otherwise,” Justin says, alongside a photo of him and Hailey sitting in a car.

Justin Bieber, Hailey Baldwin

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The two are spotted out dining in New York and New Jersey and also hang out at his residence.

Justin Bieber Birthday


Justin celebrates his 21st birthday with Hailey and other friends in the Caribbean.

Selan Gomez, Instagram, Justin Bieber


Selena, who at this point had dated Justin on and off until 2014, shocks fans by liking a video he posts that shows him hula-hooping with Hailey at Target. Friendly exes?

Hailey Baldwin, Justin Bieber, Kendall Jenner


Justin and Hailey spark engagement rumors thanks to a bogus news story, which also spurred the hashtag #CongratsJustinandHailey.

Justin Bieber, Hailey Baldwin

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The two are spotted walking together in Beverly Hills.

Justin Bieber, Hailey Baldwin, New Year's Eve 2015.


Justin and Hailey get cozy while celebrating the holiday in Anguilla.

Justin Bieber, Hailey Baldwin


Justin and Hailey don’t look too happy in paparazzi photos from their New Year’s trip to the Caribbean.

Justin Bieber, Hailey Baldwin, Instagram


The two share a passionate kiss on a night out.

Justin Bieber, Hailey Baldwin, Instagram


A source tells E! News¬†that Justin and Hailey’s relationship is¬†“more of a just a fling,” adding,¬†“They have a lot of fun together but don’t know what will happen now. They aren’t thinking too much about it and are just having fun.”

Justin Bieber, Hailey Baldwin, Friends


The two reunite in San Francisco for Super Bowl 50 Weekend.

“They are not an exclusive couple even though Hailey has made it clear that’s what she wants from Bieber,”¬†a source tells E! News. “They spent the night together Saturday.”

“All of Bieber’s friends like Hailey and would like to see them together,” the source adds. “They are dating. They both had a great time this weekend with each other.”


Hailey Baldwin, Justin Bieber, Braids, Cornrows


“Hailey made me get corn rows like an absolute douche bag, these will be off tomorrow trust me Danny,” Justin says, showing off a new look during their vacation.

Meanwhile, a source tells E! News, “Hailey and Justin have a very tight relationship. They both are very close with each other’s families and care very deeply about each other. Hailey’s family has been there and supported Justin through his transition so Justin has a strong respect for them.”

“He loves Hailey as a friend and considers her one of his best friends,” the source adds. “They both also have a strong attraction towards each other and this trip they have been having fun with their families, but also had some alone time.¬†Hailey and Justin like to party and let loose and this romantic connection has always been there.”

Justin Bieber, GQ

Eric Ray Davidson/GQ

Justin tells¬†GQ¬†magazine that Hailey is “someone I really love,” adding, “We spend a lot of time together.”

Hailey Baldwin, amfAR

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“We are not an exclusive couple. He’s about to go on tour,” Hailey tells E! News about Justin after his¬†GQ article comes out. “Relationships at this age are already complicated, but I don’t really like to talk about it because it’s between me and him.”

Justin Bieber, Hailey Baldwin, Instagram


“Hailey is not dating anyone at this time, just hanging out with her friends and working,” a source tells¬†E! News.¬†“Bieber and Hailey are still close friends, but he is on tour and extremely busy now, so they have not seen each other that much. Bieber and Hailey love each other but have a good understanding where they both stand at the moment.”


Hailey Baldwin, Marie Claire

Tesh for Marie Claire

“I don’t want attention out of dating somebody,” Hailey tells Marie Claire. “Texts started coming through, crazy phone calls…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.”

Justin Bieber, Selena Gomez, Van Nuys airport


Justin and Selena rekindle their romance.

Hailey Baldwin, Shawn Mendes

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E! News learns Hailey is dating the singer.

Selena Gomez, Justin Bieber

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The two call it quits over their romance again.

Justin Bieber

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Justin and Hailey attend the same church service together.

Shawn Mendes, Hailey Baldwin, Met Gala, 2018, Couples

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Hailey and the singer make their joint red carpet debut at the prestigious celebrity event, fueling romance rumors. They post photos of each other on Instagram.

Hailey Baldwin, Shawn Mendes


Hailey tells¬†the Times UK¬†that she and Shawn “hang out and he’s super-lovely and a very, very nice young gentleman,” adding, “But I am single.”

She also says, “Justin and I were friends for a long time. I met him when I was really young and he was one of my best friends. Everybody knows that at a certain point in time that turned into something else, but that just happens when you’re 18, 19. It was what it was. We went through a long period of time when we weren’t friends. We didn’t speak for quite some time and there was a lot of weirdness that went on. We’ve moved past that.”

Shawn Mendes, Time 100 Gala

Evan Agostini/Invision/AP/REX/Shutterstock

He¬†tells E! News,¬†“I am single. The Met Ball was such an incredible experience for me. It was just overwhelming in the most incredible way. I was so lucky for my first time going there to be able to go with someone like Hailey because she’s such a vet and I really admire people like her because of how outgoing she is in such an overwhelming experience.”

Justin Bieber, Hailey Baldwin

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Justin and Hailey reunite in Miami, sparking romance rumors again.

Hailey Baldwin, Justin Bieber

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Justin and Hailey pack on the PDA in New York City, which is captured on video.

“I don’t know if they’re dating or not,” Shawn Mendes tells¬†Canada’s¬†eTalk, adding, “I love them both. They’re both really awesome people.”

Hailey Baldwin, Justin Bieber


Justin and Hailey get cozy on the set of a music video in Los Angeles.

Shawn Mendes, Hailey Baldwin, Met Gala, 2018, Couples

Neilson Barnard/Getty Images

Hailey deletes photos of Shawn from her Instagram. He keeps his pics of the two on his own page.

Justin Bieber, Hailey Baldwin

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Justin and Hailey celebrate the holiday together in the Hamptons.

Hailey Baldwin, Justin Bieber

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Justin and Hailey head back to New York City for a romantic weekend.

Check out an extensive timeline of their romance and road to engagement.

Don’t miss¬†E! News¬†every weekday at 7 and 11 p.m.


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