With the news of Justin Bieber's recent engagement to Hailey Baldwin still making the rounds, there’s a lot to think about. However, one thing is clear: Justin is officially off the market. It’s been a long time coming for the pop superstar, who has been linked to everyone from Miranda Kerr, Adriana Lima and Kendall Jenner. Oh, and we obviously can’t forget his on-again-off-again romance romance with Selena Gomez. In honor of the Biebster’s big news, iHeartRadio has decided to take a trip down memory lane to revisit the singer’s romantic life. After all, it sometimes takes time to find your way to the one.
Caitlyn Beadles (2009)
Beliebers will tell you that Beadles was Bieber’s first girlfriend. She was the older sister of his then-best friend, Christian Beadles. The two met when Bieber made his first move from Ontario, Canada to Atlanta, Georgia while his career was taking off. However, their love story quickly ended when Bieber's tour schedule became too much for the couple to handle.
Kristen Rodeheaver (2009)
Kristen Rodeheaver was the star of Bieber’s first music video, “One Time.” Rumors of the two being more than friends surfaced after the filming of the clip.
Mandy Rain (2009)
In 2009, Bieber met Rain after making a guest appearance in the School Gyrls movie. Word on the street is the pair became romantic after filming.
Jessica Jarrell (2010)
Jarrell hit the road with the Biebster throughout the duration of his “My World Tour” after being featured on multiple songs on his My World EP. After the two held hands during a performance, the public jumped on the moment and concluded that they were a couple.
Jasmine Villegas (2010)
Villegas was Bieber’s love interest in the music video for “Baby,” and sometimes life imitates art. Back then, the two described their relationship as "just cool friends" while making the press rounds, but they were spotted out and about being much more than just friends.
Barbara Palvin (2012 & 2014)
These two allegedly had a fling after Bieber performed at the 2012 Victoria's Secret Fashion Show in New York City. At the time, Bieber was still dating Selena Gomez, so it’s no surprise that the pairing caused tension on Twitter. Two years later, the two were seen together at the 2014 Cannes Film Festival.
Miranda Kerr (2012)
Bieber and Kerr also sparked hookup rumors in 2012 during the filming of the Victoria’s Secret Fashion Show. However, in 2014, Kerr’s attorney made a statement, revealing that the rumors were “false and defamatory.” The rumors also sparked trouble between Bieber and Orlando Bloom (Kerr’s then husband), causing a physical altercation between the pair at a restaurant in Ibiza, Spain.
Milyn Jensen (2013)
In 2013, the nursing student and wannabe model spoke out about spending a night with Bieber and it caused some major drama. In an interview, Jensen said, “[Justin and I] were kissing and I started to take off my clothes, it was a natural thing... Justin knew what he was doing, like a man much older than his years. I felt like he'd had a lesson or two." This hookup is said to have been the reason for Bieber and Gomez’s 2013 breakup.
Ella-Paige Roberts-Clarke (2013)
Bieber was also once spotted with Roberts-Clarke, a British singer-model, at Justin Timberlake’s 2013 BRIT Awards afterparty.
Jacque Rae Pyles (2013)
Bieber and Pyles also met in 2009 on the film set of School Gyrls. The two sparked dating rumors when they were spotted boarding a private jet to Las Vegas for the Mayweather/Alvarez boxing match. Recognize the girl on the right? Probably because Mandy Rain is also on the list from her brief fling with Bieber back in 2009.
Tati Neves (2013)
This Brazilian model became an overnight sensation when she posted a video of Bieber sleeping in a hotel bed. She later reported that the two spent the night together. After the video went viral, Neves appeared in interviews and made the big claims that they were intimate.
Chantel Jeffries (2014)
Bieber and Jeffries were together in early 2014. The highlight of the relationship arrived when Jeffries’ Instagram was hacked and a nude photo of Justin was posted, with Selena Gomez tagged on the post. After about 20 minutes, the post was taken down and declared photoshopped. The two split later that year after Jeffries was present for Justin’s 2014 DUI arrest. Jeffries may look familiar since she is pictured above with Ella-Paige. Guess it's safe to say best friends do share everything.
Jordan Ozuna (2014)
Ozuna and Bieber spent Valentine’s weekend together, while Selena spent the weekend with former One Direction member, Niall Horan. Talk about a love triangle!
Kylie Jenner (2014)
Many have speculated that Jenner sent some scandalous pictures to Bieber around the time of Coachella. Imagine what would have happened if Bieber made himself comfortable in the Kardashian circle.
Adriana Lima (2014)
After her separation with Marko Jaric, Lima found herself in a hookup rumor with Bieber when the two were spotted partying at 1OAK during the Cannes Film Festival. In December 2015, Lima put the rumors to rest. “OK, I’m going to tell you this. Anybody below 6-foot-7, you know how I call them? Friends,” she admitted. Bieber is 5-foot-9, which put him in the friend zone.
Yovanna Ventura (2014)
After posting romantic pictures with Ventura, Bieber found himself in another romance and this one lasted for five months. Interestingly enough, the news surfaced days after Bieber and Selena were spotted together at Alfredo Flores’ birthday party. Bieber was reportedly helping Ventura with her modeling career. She is currently still modeling and has 5.2 million Instagram followers.
Alyssa Acre (2014)
In August 2014, Justin and Alyssa, a Playboy Playmate, were rumored to be dating after they were spotted making out on a yacht in Ibiza.
Kendall Jenner (2014/2015)
These two were rumored to be together after another Jelena breakup in fall 2014, courtesy of some suggestive Instagram photos together. In 2015, Kendall reported that she had a 12-year-old crush on Bieber, but it ended there.
Jayde Pierce (2015)
Pierce was the mystery girl who spent time with Bieber in Bora Bora in 2015 when the nude photos of him on the balcony went viral. Six months after the couple broke up, Pierce announced that she was expecting her first child with rapper, Mike Dixon.
Ashley Moore (2015/2018)
Moore was a model who was spotted getting cozy with Bieber at a Clippers game in Los Angeles. Moore was spotted hiking with Bieber in February 2018.
Shanina Shaik (2015)
The two were first linked to one another after Justin and Selena’s 2014 break-up. They were seen attending the Mayweather/Pacquiano fight in Las Vegas in 2015. Afterward, Bieber posted two Instagram photos with Shaik after their weekend together. Today, Shaik is a Victoria’s Secret model and engaged to DJ Ruckus.
Bronte Blampied (2016)
The Australian model is said to be have come into the picture right between the Hailey Baldwin and Sofia Richie eras. The two were most recently spotted in early 2018 having lunch in Australia.
Sofia RIchie (2016)
There was never a dull moment with this summer romance. After posting a picture with Richie, fans started getting feisty and eventually Selena had something to say about the shots. Richie described her relationship with Bieber to Billboard as “special.” “He was just very easy to talk to, and that’s hard to find with people in Los Angeles,” she said. Not long after the interview, the couple broke things off. A year later, Richie started dating Scott Disick.
Selena Gomez (2010-2018)
When these two were first spotted together at a Philadelphia IHOP, they were reportedly just enjoying a friendly hangout with one another. The two went public as a couple at the Vanity Fair Oscars Party in February 2011, prompting Gomez to speak about their relationship in Seventeen. After almost seven years of their on-again-off-again romance, the two reunited in October 2017 and were spotted getting breakfast at a cafe in Westlake Village, California. In March 2018, an insider confirmed that Bieber and Gomez were going to be taking a “breather."
Hailey Baldwin (2011-2018)
In February of 2011, 14-year-old Hailey joined her father, Stephen Baldwin, and 16-year-old Bieber on the red carpet for the premiere of his biopic “Never Say Never’ in New York City. Years down the line in November 2014, the two were photographed together for the first time in years with Kendall Jenner at Hillsong Church in NYC. After the photos together, relationship rumors began buzzing, but Baldwin shut them down. "People are crazy. I'm super single and this is my good friend u would know otherwise,” Bieber told Instagram followers. In 2015, the two celebrated New Years together, denying any kind of relationship. The two also brought in 2016 and shared a photo of them kissing in early January via Instagram. In August 2016, the two called it quits. After a tense breakup, and not speaking to one another for some time, the two were spotted once again in June getting cozy together in Miami and New York. On July 8, TMZ was the first to report that Bieber and Baldwin were engaged after the singer popped the question during their vacation in the Bahamas.