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.
November 2014: Birthday Girl
Hailey celebrates her 18th birthday with Justin and other friends, such as Kylie Jenner and Kendall Jenner. No romance rumors yet.
December 2014: Rumors Begin
Hailey and Justin appear together in Instagram pics, sparking romance rumors.
“I’ve known him since I was so young—since I was like 13—and 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.”
December 2014: “People Are Crazy”
“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.
Late December 2014: East Coast Hangouts
The two are spotted out dining in New York and New Jersey and also hang out at his residence.
March 2015: Birthday Boy
Justin celebrates his 21st birthday with Hailey and other friends in the Caribbean.
April 2015: Hi, Selena Gomez
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?
Late April 2015: Engaged???
Justin and Hailey spark engagement rumors thanks to a bogus news story, which also spurred the hashtag #CongratsJustinandHailey.
The two are spotted walking together in Beverly Hills.
December 2015: New Year’s Eve PDA
Justin and Hailey get cozy while celebrating the holiday in Anguilla.
January 2016: Trouble in Paradise?
Justin and Hailey don’t look too happy in paparazzi photos from their New Year’s trip to the Caribbean.
January 2016: False Alarm..and PDA Alert!
The two share a passionate kiss on a night out.
January 2016: Just a Fling?
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.”
February 2016: Super Bowl Fun
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.”
January 2016: Braids and a “Tight Relationship”
“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.”
Eric Ray Davidson/GQ
February 2016: “Someone I Really Love”
Justin tells GQ magazine that Hailey is “someone I really love,” adding, “We spend a lot of time together.”
Michael Loccisano/Getty Images
February 2016: “We Are Not an Exclusive Couple”
“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.”
March 2016: Hailey Is “Not Dating”
“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.”
Tesh for Marie Claire
April 2016: “It’s Hard to Date Somebody in This Industry”
“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.”
ROMA / MEGA
Late Fall 2017: Re-Enter Selena Gomez
Justin and Selena rekindle their romance.
Dominique Charriau/WireImage, Jason Merritt/Getty Images
November 2017: Enter Shawn Mendes
E! News learns Hailey is dating the singer.
March 2018: Justin and Selena Split
The two call it quits over their romance again.
Max Lopes- Vasquez / BACKGRID
Late March 2018: Church Reunion?
Justin and Hailey attend the same church service together.
Neilson Barnard/Getty Images
May 2018: Hailey and Shawn Mendes at the Met Gala
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.
Late May 2018: Hailey Is Single
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.”
Late May 2018: Shawn Mendes Is Single
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.”
Splash News / BACKGRID
June 2018: Reunion in Miami
Justin and Hailey reunite in Miami, sparking romance rumors again.
Mid-June 2018: NYC Kisses
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.”
Late June 2018: More PDA
Justin and Hailey get cozy on the set of a music video in Los Angeles.
Neilson Barnard/Getty Images
Late June 29 2018: Bye Shawn Mendes
Hailey deletes photos of Shawn from her Instagram. He keeps his pics of the two on his own page.
247PAPS.TV / SplashNews.com
July 2018: Fourth of July
Justin and Hailey celebrate the holiday together in the Hamptons.
Spartano / BACKGRID
July 2018: Back to NYC
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.
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