After the two insisted that they were just friends, things seemingly went to the next level during a New Year's Eve 2015-16 vacation in Anguilla. Justin shared a photo of Hailey and himself locking lips on Instagram, as well as a photo of the two dressed to go out. Hailey told E! News, "We are not an exclusive couple... relationships at this day and age are complicated." The pop singer and model's paths crossed once again in 2018, and surprised fans when E! News confirmed Bieber had proposed to his on-again love in July while vacationing in the Bahamas.
A love story that will go down in Hollywood history! The two spent close to half a decade trying to figure out if they were better off together or apart, up until March 2018 when a whirlwind reunion ended in flames. Jelena forever? Not so much.
Rebound alert! Following his split from Gomez, Bieber casually dated the social media sensation for several months, who he met through mutual friends. "He really liked hanging with Baskin because she was down to earth and laid-back, but the distance has definitely been a factor," explained an insider of their ultimate breakup.
In the fall of 2017, Bieber struck up a romance with the brunette model. Their fling was short-lived, but a source at the time shared, "Justin likes how well diverse and smart she is. They are having fun and enjoying each other's company."
In 2016, the budding model and celeb spawn (her dad is Lionel Richie), was spotted on the beach with Bieber and then made a very poorly received cameo on his Instagram, which ultimately resulted in Justin deleting his account.
"Justin has a crush on Nicola and really enjoyed the date with her the other night," an insider shared after the pair was spotted out on the town in 2016. "He wants to settle down and have a relationship. He feels like something steady would be good for him."
The fashion design student and swimsuit model was, ironically, photographed skinny-dipping with Justin in Hawaii not long before he started hanging out with Sofia Richie in 2016.
These two were the subject of rumors for months in 2014, but the model and Keeping up with the Kardashians star has maintained that Justin is just "a friend of the family."
And that goes for big sister too. The newly single Kardashian and Bieber were everyone's favorite rumor for a hot second in 2015, but Kourtney always maintained they were just friends. Justin joked once that he was "being used," but quickly added, "No, no, but for real, she's great. I've known [her family] for years."
The model was hanging out with Bieber and friends when he got a DUI in 2014 in Miami. Their relationship lay dormant for a while, but in July 2016 Bieber gave her tickets to one of his shows at Madison Square Garden and they had a private movie date afterward.
The Victoria Secret Angel denied ever dating Justin back in 2014, but a source told E! News they had a brief fling that year in Cannes. "Anybody below 6-foot-7, you know how I call them? Friends," Lima told Andy Cohen on Watch What Happens Live in 2015.
Calling all Angels, while we're at it. Sources have said that Bieber pursued Kerr after meeting her in 2012, and they would text here and there over the years, but "she didn't entertain his attempts at making steady contact." Fast-forward to 2014 when Bieber and Kerr's ex Orlando Bloom got into a fight in Ibiza, supposedly triggered by a remark Bieber made about Kerr.