So Many Less Lonely Girls: Looking Back at Justin Bieber's Stacked Dating History Before Finding the One

Before there was Hailey, there was Selena, Jasmine, Baskin and more than a few Angels

By Tierney Bricker Mar 01, 2019 11:00 AMTags
Justin Bieber, Dating HistoryBackgrid; Getty Images/E! Illustration

If I was your boyfriend, I'd never let you go."

So sang Justin Bieber in his 2012 hit song "Boyfriend," but judging from his pretty stacked dating history, we think we can safely say that the sentiment, while sweet, wasn't exactly true. 

Justin, who turns 25 on March 1, has definitely stepped into the role of boyfriend more than a few times since becoming one of the biggest stars on the planet back in 2009, when he was just 15 years old. 

Through the ups and downs, hookups and breakups, Justin finally managed to settle down with Hailey Baldwin, whom he married in a surprise ceremony in September 2018 after three years of on-and-off dating. 

Looking Back on Justin Bieber's Stacked Dating History

But before he found The One, there were more than a few less lonely girls, a defining Young Hollywood romance with Selena Gomez, and even more struggles for Justin to go through, with his every move, relationship and mistake being documented and dissected by the public.

"A lot of the douchey things I was doing gave people the right to be like, Man, that's frickin' douchey, bro. But a lot of the stuff was like—me peeing in a bucket, people made such a big deal of that. Or me owning a monkey. It's like, if you had the money that I had, why wouldn't you get a monkey? You would get a monkey!" Justin explained to Vogue earlier this year, revealing he was abusing Xanax and had a "legitimate problem with sex" before changing his ways.  "I found myself doing things that I was so ashamed of, being super-promiscuous and stuff, and I think I used Xanax because I was so ashamed. My mom always said to treat women with respect. For me that was always in my head while I was doing it, so I could never enjoy it." 


And he admitted to struggling with fame and dealing with the impact it inevitably has on your ego, especially in your formative years, something he is still working to unpack. 

"I was real at first," Justin said, "and then I was manufactured as, slowly, they just took more and more control." It felt fantastic to be famous, to be adored by girls. At sixteen, he blindly believed the hype. "I started really feeling myself too much. People love me, I'm the shit—that's honestly what I thought. I got very arrogant and cocky."

Justin Bieber and Hailey Baldwin's Cutest Pics

Eventually, Justin canceled his 2017 world tour and took a step away from the music industry as he realized he "just needed some time to evaluate myself: who I am, what I want out of my life, my relationships, who I want to be—stuff that when you're so immersed in the music business you kind of lose sight of." 

Which ultimately lead him to Hailey, who officially changed her name to Hailey Bieber in November 2018.

And as Justin continues to struggle with depression, a source told E! News Hailey, 22, has been a solid support system for her husband.

"He really wants to get better," the insider shared. "He has been seeking all the help he can get."

It's been a long road to happily ever after for the young couple and for Justin; let's look back on his dating history before getting married to his "baby boo"...

First Girlfriend

Back in 2008, Justin met his first girlfriend Caitlin Beadles when he moved to Atlanta to work with Usher. They dated for about a year, with Caitlin reportedly ending things as Justin's fame was growing, and "Never Let You Go" off my My World 2.0 is allegedly inspired by her. 

The two have remained friends over the years as Justin is also friends with her brother, Christian, and the "Boyfriend" singer even spent Thanksgiving 2017 with their family. 

Christian posted a photo of the trio from their holiday celebration, writing, "So thankful for my brother and sister this thanksgiving #happyturkeyday #family."

Puppy Love

Before his epic romance with Selena, Justin, then 15, dated Jasmine Villegas, who was featured in his 2010 "Baby" music video (how they met!) and then was one of the opening acts on his My World tour.

The pair dated for nine months (January-September 2010), with Jasmine later saying, "It was like a little kid thing, it was like puppy love, if you could even call it that."

As for how they got together, Justin actually had to ask Jasmine's mom for her phone number. "It was really nice, he has to ask my mom because my mom stood by me on the whole set, so I don't think he could've got past her if he tried!"

After they broke up, with Jasmine saying it was never a "serious" relationship, they remained friends.

Jelena Is Official

While fans had hoped for the pair to be dating after Justin had confessed that the Wizards of Waverly Place star was his crush, Selena had seemingly shot down any chance of a real romance when she once told Ellen DeGeneres, "He's little. He's like my little brother."

But when they were photographed kissing on a romantic vacation in the Caribbean, it was clear her feelings had changed for the pop star two years her junior.

But the duo made it red carpet official and caused a frenzy when they attended the Vanity Fair Oscar party together.

"I am happy," Selena told E News of their romance. "I'm really happy."

Of course, given his status as the ultimate teen dream at the time, some of Justin's fans were less than nice to his new girlfriend on social media, something Selena admitted to struggling with.

"It hurts, it really does," she once told Z100 radio. "I don't feel like I'm doing anything wrong. I've been best friends with him for a very long time. It does hurt my feelings a lot, but I try not to focus on it."

The First Heartbreak

E! News was the first to report in November 2012 that the young Hollywood power couple had split up after weeks of speculation, including cryptic social media posts.

"Because of their crazy schedules, it was getting harder and harder to maintain a relationship," a source said at the time.

Playing With an Angel

Justin seemed to move on pretty quickly after his split as he was spotted going to a Broadway musical (The Lion King) with model Barbara Palvin, the day after he performed at the 2012 Victoria's Secret Fashion Show, which she walked in.

After photographs of the pair out in NYC caused a stir online, Barbara took to her Twitter to address the rumors.

"last time im saying it. please calm down.there is nothing going on w him.i met him and did a pic w him," she wrote. "wouldnt u do the same?:) #friendship."

And yes, Barbara is now happily dating Dylan Sprouse, another one of your childhood crushes, so she's living the suite life. 

Another Angel

Here's some pretty good gossip nostalgia for you: After that same Victoria's Secret Fashion Show performance, rumors also began circulating that Justin had hooked up with Miranda Kerr, who was then married to Orlando Bloom. Not amused by that rumor? Miranda's lawyers, who quickly released letter saying that any implications of their client hooking up with the bad boy singer were "false and defamatory."

Fast-forward two years later when Orlando allegedly took a swing at Justin at a restaurant in Ibiza after the "Sorry" singer allegedly made a comment about Miranda, who Orlando had split from the previous year. It also went down after Orlando was spotted hanging out with Selena Gomez. Talk about a throwback love square.

Yet Another Angel

Justin clearly has a thing for wings, as he reportedly hooked up with Victoria's Secret angel Adriana Lima while they were both at the Cannes Film Festival.

And yet, Adriana show down the rumors and threw shade at Justin when she later appeared on Watch What Happens Live when Andy Cohen asked about the alleged hookup.

"Anybody below 6'7", you know how I call them?" she asked. "Friends."

Oof, anyone have some aloe to offer Justin to soothe that burn? 

Buckle Up

Well, it wasn't the best way for the news of a potential new romance to get out as Chantel Jeffries was linked to Justin after he was arrested for drunk driving and drag racing in Miami in January 2014, and she was sitting in the passenger seat. 

Of course, the media soon reported everything about Chantel, including her own alleged arrest history.

"I have been overwhelmed by the negative attention I have recently received in the media," the model told E! News in a statement at the time. "My family and I are particularly upset about the false accusations which have been published concerning my criminal history."

After he was released from jail, the pair traveled to Panama and helped him celebrate his 20th birthday, but the romance eventually fizzled out.

Keeping Up With a Kardashian

Justin and Kourtney Kardashian make headlines in the fall of 2015 after they are spotted hanging out together, including going to Halloween Horror Nights at Universal Studios together after her high-profile split from Scott Disick over the summer.

Justin is a longtime friend of the Kardashian fam, so people weren't sure if Kourtney, 36, and Justin, then 21, were just friends or maybe had become friends with benefits.

Justin later addressed the rumors, saying, "I'm being used, man. What can I say?" when asked about the headlines.

He then added, ""No, no, but for real, she's great. I've known [the family] for years."

When pressed on if there was anything going on between them, Bieber simply said, "Nah, we'll leave it at that."

OK then!

Bieber Nabs a Baldwin

Justin made his relationship with Hailey Baldwin, the model daughter of actor Stephen Baldwin, Instagram official in January 2016, when the pair was on vacation together and he posted a steamy pic of the couple kissing. (This came after months and months of social media posts and outings suggesting they were a couple.)

The pair actually met back in 2009 at the Today show (in a clip that lives online in all of its awkward infamy!) after she received tickets from her uncle, Alec Baldwin, going on to later develop a friendship through the Hillsong church. 

"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," a source told E! News. "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 added. "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."

And looking back on an insightful profile of the troubled singer for GQ, there's quite a telling nugget in the piece: The writer noted that Hailey was waiting for Justin in his hotel room, but Justin wouldn't confirm they were dating; he just said she was "someone I really love. We spend a lot of time together."

But here's the important part, the one that foretold a lot: explaining his hesitance to settle down at that point in his life, Justin said, "What if Hailey ends up being the girl I'm gonna marry, right? If I rush into anything, if I damage her, then it's always gonna be damaged. It's really hard to fix wounds like that. It's so hard…I just don't want to hurt her."

Dramatic Split

While the details of their breakup in 2016 were never made public, it was clearly not a pretty one. 

"Negative things happened that we still need to talk about and work through," Hailey explained to Vogue for the pair's joint cover story in February 2019. "Fizzled would not be the right word—it was more like a very dramatic excommunication. There was a period where if I walked into a room, he would walk out."

But at the time, Hailey downplayed any drama, telling E! News back then, "We are not an exclusive couple. He's about to go on tour. Relationships at this age are already complicated, but I don't really like to talk about it because it's between me and him."

Dinner Date

While they never officially dated, Justin was spotted going on a date in Beverly Hills with Transformers star Nicola Peltz in May 2016.

"They are not a couple, they just went on a date. Justin thinks she is really pretty, though," a source spilled to us. "Justin is single at this moment."

Chantel 2.0

Justin and Chantel briefly rekindled their romance in the summer of 2016, with the model attending one of his concerts in NYC.

"Chantel and Bieber have been hanging out for the past few months," an insider told us. "Last night Chantel went to see Bieber in concert. Bieber got [her] tickets."

But it was their own private after-party after that made headlines, as Justin rented out an entire theater at AMC Theaters in Times Square so they could watch a movie together.

"Bieber likes Chantel. He thinks she is a great girl," our source said at the time. "Chantel would really date Bieber exclusively if he was ready. They have been good friends for a while."

Alas, it seems like Justin was never ready to be exclusive.

Short and Sweet

Another lady, another quasi-love square for Justin.

Before she ended up dating Scott Disick, Sofia Richie was linked to Justin in the summer of 2016.

The pair made headlines when they celebrated her 18th birthday with a trip to Mexico, thought sources at the time stressed they were never labeled their relationship.

But Justin still publicly defended Sofia after his followers began attacking her and leaving mean comments on her Instagram.

"I'm gonna make my Instagram private if you guys don't stop the hate this is getting out of hand. If you guys are really fans you wouldn't be so mean to people that I like," he wrote on Instagram.

(Curiously enough, Selena weighted in, though she later deleted her comment, which allegedly read, "If you can't handle the hate then stop posting pictures of your girlfriend lol – it should be special between you two only. Don't be mad at your fans. They love you.")

"We have a special relationship," Sofia said when asked about Justin. "Justin is very easy to talk to, and that's hard to find with people in Los Angeles."

But it was a shortlived romance, as Justin ended things in September.

"They were never officially together, but more casual hanging out and having fun," a source said. "It was super-hot and heavy, and because Justin doesn't want a relationship right now, he wanted to cool things down."

Jelena Is Back On

In November 2017, Justin and Selena once again rekindled their romance after her breakup with The Weeknd the month prior after over a year together.

Fans first knew something was up when Selena was spotted kissing Justin at one of his hockey games, a lip-lock that confirmed several hangouts following her kidney transplant surgery earlier in the year.

"They are exclusive," a source told us. "They don't want to date anyone else. They both are very committed to making this work. Justin and Selena have grown up since the last time they were together."

The pair allegedly reconnected through their church, though Selena's family and friends were concerned after Justin's previous behavior.

"Her family and friends just don't want Selena to be with the immature and foolish Justin they know," the source added. "He's trying to change and be a better guy. We'll see what happens...Justin is changing but it's a process. He's trying."

The Final Breakup

In early March, sources confirmed to us that Selena and Justin were taking some time apart after taking several trips together during their reconciliation including a trip to Jamaica to attend his father's wedding.

An insider explained, "They were having a lot of little disagreements recently and one fight in particular blew up and caused them to decide to 'break up,' however, they've been in contact the entire time and their feelings for each other have not changed."

And the source added they wouldn't be surprised if the pair reconciled once again, but were feeling "overwhelmed with a lot of the pressure that has come with their public relationship."

Another sticking point? Selena's mother Mandy Teefey was reportedly "not happy" her daughter wsa dating Justin again.

Moving On

Though sources had told us not to rule out a reconciliation with Selena, Justin started casually dating model Baskin Champion in March 2018 after they were introduced by his good friend Patrick Schwarzenegger, who is dating Baskin's sister Abby Champion.

The couple was spotted attending a Craig David concert together and going to SoulCycle, with a source telling us, "Justin seems very into Baskin and like they are very comfortable together. They are having fun and always laughing and flirting."

After just three months though, their romance fizzled out.

"It was never a serious relationship, but they haven't hung out in over a month," a source shared with E! News at the time. "He really liked hanging with Baskin because she was down to earth and laid-back, but the distance has definitely been a factor."

Still, Justin wanted "to remain friendly" with Baskin.

The Unexpected Reconciliation

In June 2018, Justin and Hailey unexpectedly reunited at a conference hosted by pastor Rich Wilkerson Jr. in Miami, but the "Love Yourself" crooner had no interest in just being friends again.

"The common denominator, I promise you, is always church. By then we were past the drama. I just gave him a hug," Hailey revealed to Vogue. "By the end of the conference, he was like, 'We're not going to be friends.' I was like, 'We're not?' "

From then on, the reconciled couple was attached at the hip. And within a month, they were engaged, as Justin proposed during a trip to the Bahamas.

"They are engaged and it happened Saturday night in front of a crowd in Baker's Bay," a source told E! News exclusively. "Justin made arrangements for the ring when they were in NYC and knew that he wanted to propose to her. It was a sudden decision but Justin always knew Hailey and him had a special bond that was incomparable."

Surprise Nuptials

By September of 2018, Justin and Hailey were officially Mr. and Mrs. Bieber, exchanging vows in a small courthouse ceremony in NYC (with a bigger wedding slated to happen sometime this year). 

The couple "didn't tell anyone they were doing it," a source told E! News, "They are doing a separate ceremony out of the country with a few family members soon as well."

While some felt the young couple had rushed into marriage, Hailey told Vogue she took the decision quite seriously. "I prayed to feel peace about the decision, and that's where I landed," she explained. "I love him very much. I have loved him for a long time."

For Justin, who had chosen to be celibate for over a year before the pair reconnected as he had "a legitimate problem with sex," he knew Hailey was in fact the one as soon as they saw each other again.

"When I saw her last June, I just forgot how much I loved her and how much I missed her and how much of a positive impact she made on my life. I was like, Holy cow, this is what I've been looking for."

"Baby Boo"

In their Vogue cover story, the newlyweds didn't hide the fact that marriage is hard, especially when you are young, wealthy and have completely different personalities.

Calling himself the "emotionally unstable one," the more careful and serious Hailey is a much-needed constant. 

"'With the lifestyle I live, everything is so uncertain. I need one thing that's certain. And that'—he picks up her hand—'is my baby boo,'" the magazine detailed.

And Hailey is just as serious about Justin as she is their marriage, telling Vogue, "We're really young, and that's a scary aspect. We're going to change a lot. But we're committed to growing together and supporting each other in those changes. That's how I look at it. At the end of the day, too, he's my best friend. I never get sick of him."

For more on the young couple's romance, here's everything we know about Justin and Hailey's impending wedding celebration...