Canadian singer Justin Bieber is slated to marry model Hailey Baldwin after popping the question Saturday.
Bieber’s engagement to Baldwin, which first made headlines Sunday, came after the pair rekindled their off-and-on-again relationship in May. The “What Do You Mean” singer, 24, proposed to the 21-year-old model while eating dinner at a restaurant in the Bahamas. Before the proposal, the pair dated from late 2015 to early 2016.
Bieber has been linked to multiple well-known names in Hollywood. He’s been rumored to have sparked romances models like Adriana Lima and Miranda Kerr. His “nice friendship” with singer Ariana Grande—who shares manager Scooter Braun with Bieber—was once said to be a factor in her breakup with Big Sean. Here’s a list of all of Bieber’s most noteworthy romantic associations prior to proposing to Baldwin.
Selena Gomez is Bieber’s most notable former girlfriend. The Disney alum initially called Bieber her “little brother,” but later publicized their relationship in 2010 before concluding it in 2012. Since then, the pair earned the name “Jelena” and dated off-and-on until March. Gomez spoke with Billboard in December after they reconnected, saying: “I’m 25. I’m not 18, or 19, or 20. I cherish people who have really impacted my life. So maybe before, it could have been forcing something that wasn’t right.”
Before Sofia Richie dated Scott Disick, the 19-year-old model, the daughter of singer Lionel Richie was involved with Bieber in 2016. During their relationship, the pair suffered a wave of social media backlash from fans—resulting in Bieber briefly deleting his Instagram. Although Richie said they had a “special relationship,” they parted ways after roughly six weeks.
Kendall Jenner and Bieber have maintained that they’re simply friends, but the pair sparked dating rumors after Jelena’s 2014 breakup. Speculation regarding the pair’s relationship surfaced again in 2015 after Bieber shared questionable photos of the duo to Instagram. “He’s a longtime friend of our family,” Jenner, now 22, told ABC’s Nightline in 2014. “Everybody loves to assume things, but no.”
Jenner isn’t the only member of the Kardashian-Jenner clan that’s been linked to Bieber. In December 2015, Kourtney Kardashian and Bieber were spotted out together on multiple occasions, including a visit to Universal Studios. “I’m being used, man. What can I say?” Bieber jokingly said on The Bert Show at the time. “We’ll leave it at that…. For real, she’s great.”
Chantel Jeffries, a YouTube personality turn music star, was first seen with Bieber in 2014. During their time together, Jeffries was arrested alongside the singer following his drunk drag racing in Miami. Jeffries briefly reconnected with the “Boyfriend” star in 2016. She’s since been suspected as the inspiration behind Bieber’s “Love Yourself,” but YouTuber Jayde Pierce has also be positioned as the track’s presumed subject.
Barbara Palvin, a model, was rumored to be hooking up with Bieber after they were spotted attending The Lion King on Broadway in November 2012. The pair first met a day prior at the Victoria’s Secret Fashion Show. They were later seen together in a since-deleted photo on Lil Twist’s Twitter account that was subsequently shared by Bieber’s then-girlfriend, Gomez. “You know how the drama started—Selena retweeted the picture,” Palvin, now 24, told Celebuzz at the time. “I’m okay to talk about it because I know there’s nothing.”
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