Hailey and Justin first met as teens during a meet-and-greet in 2009 and slowly became friends afterward, being photographed on the red carpet together at the premiere of Bieber’s Never Say Never biopic in 2011. In February 2015, the two were spotted going on dates and posting photos together as they gave romance a shot. The two eventually split, but we all know how this story ends.
It’s not 100 percent clear that these two seriously dated, but People reported that the couple was casually seeing each other. They were caught cozying up with each other at parties and appearing everywhere together, but nothing was ever confirmed by the two.
April-June 2017: Cameron Dallas
It makes sense that these two models were into each other. They’re both signed to IMG and have been in the same friend group for some time. Things burned fast though, as it was reported that this relationship barely lasted more than a month.
October 2017-May 2018: Shawn Mendes
Shawn and Hailey have given a myriad of different answers about their relationship. A number of sources have reported that the two were a couple and they were spotted holding hands a number of times, but neither has ever publicly confirmed anything. Their relationship seems to have peaked at the 2018 Met Gala in May, when Hailey asked Shawn to be her date. Sadly for all the Shailey fans, things fizzled out not long after the gala. Mendes doesn't seem to mind though.
June 2018-Present: Justin Bieber
After two years apart, Justin and Hailey were caught kissing in Brooklyn. When the news broke, the couple was everywhere. They went on dates, held hands around New York together and took a vacation to the Bahamas. Much to everyone's surprise, Justin proposed to Hailey about a month into their rekindled relationship. No one can deny how happy they look together.