From Childhood Friends to Hollywood Romance: The Unexpected Journey of Hailey Baldwin and Justin Bieber
Hailey Baldwin first met Justin Bieber through her dad, actor Stephen Baldwin, who was friends with Justin’s mom. Hailey was only 12 years old, and Justin was 15. That initial meeting didn’t lead to anything significant, but two years later, they were photographed together in New York with Hailey’s dad at the 2011 premiere of Justin’s “Never Say Never” documentary.
In an interview with Vogue, Hailey confessed she wasn’t a Belieber back then. “I didn’t think about it in any kind of way except for the fact that he was cute. Everybody had a crush on him, but for the first few years, we had a weird age gap,” she said. At that time, Justin was romantically involved with Selena Gomez.
In May 2011, Hailey, showing her playful side, tweeted, “I don’t care what anyone says, but Justin Bieber and Selena Gomez together is the definition of a teenage dream.” Later, internet detectives dug up Hailey’s old tweets, including one from January 2012 where she complimented Justin’s dark hair, but he was too busy to reply. Meanwhile, Justin and Selena experienced a rollercoaster relationship with numerous breakups and reconciliations.
In 2014, Justin Bieber got arrested for DUI, and Selena Gomez checked into rehab for lupus treatment. That same year, Justin was seen at a church service with Hailey Baldwin and Kendall Jenner. Hailey later told Vogue that their friendship started from that point, calling Justin her “best guy friend.” She said, “I was running around with him as his homie, but we weren’t hanging out romantically.”
Fans were buzzing with rumors that Justin was leaving Selena behind. He tried to clear things up on Instagram, saying he was single and Hailey was just a friend.
Despite spending New Year’s Eve together, Justin and Hailey insisted their relationship was just friendly. For Justin’s 21st birthday, he and some friends, including Hailey and his on-again, off-again fling Yovanna Ventura, went to a private island in the Caribbean. According to Hollywood Life, Hailey left the island abruptly because Justin was getting too close to Yovanna. An insider said, “She says she’s cool with him being with other girls, but putting it in her face like that was too much.” When someone online asked Hailey if she left because Justin was being a jerk, she confirmed she left but said, “I didn’t have to leave for that. I left because I wanted to.”
By the end of 2015, Justin was seen serenading Selena. A few weeks later, Hailey joined him and his family for New Year’s celebrations, and this time, they were caught kissing.
By February 2016, Justin told GQ magazine that he really loved Hailey, but he wasn’t ready to commit to anyone. He admitted, “I know that in the past I’ve hurt people and said things that I didn’t mean just to make them happy in the moment, so now I’m more focused on the future and making sure I’m not causing harm.”
Hailey seemed okay with their casual relationship. She told E! News they weren’t exclusive because relationships at their age were too complicated. By August 2016, they were done. Hailey revealed to Vogue magazine that their breakup was a very dramatic split. She even mentioned there was a time when if she walked into a room, Justin would leave.
Justin moved on with Sofia Richie and started posting photos of her on his Instagram, but it turned out Sofia wasn’t the one. Justin and Selena reconnected again, only to break up again in March 2018. A source told People magazine they were taking a break to focus on their spirituality.
What does that even mean? Just three months after breaking up with Selena, Justin got back together with Hailey. A month later, he proposed. Wait, what? Chad, this is giving me whiplash.
Hailey shared, “When things came back around for him and me, I had really let it go. I thought, ‘I don’t know what’s going to happen with this person. I just know I want him in my life forever in some capacity, whether as a friend or more. I just love him and want to support him. He’ll always matter to me.'”
After getting engaged, they moved into Justin’s home outside Toronto and started couples therapy right away. Smart move. Hailey explained, “We had a lot of hurts between us from the stupid things we did when we were upset, jealous, and annoyed. These things needed to be healed and fixed before we could get married.”
It seemed like Hailey’s patience had paid off. She stayed while Justin explored other relationships and agreed to marry him as soon as he proposed with a sparkly ring. But little did she know, saying yes to the proposal would come with a lot of drama.
Justin opened up to Vogue about how his past caught up with him in a big way. He confessed to years of living fast – partying hard, using drugs, and being a bit of a womanizer. But all that lifestyle led to was deep depression. He admitted feeling ashamed of his past actions, especially the reckless behavior and relying on Xanax to cope with it all.
Getting clean was a turning point for him, and just before he and Hailey tied the knot, he took some time off to be celibate. They were eager to commit, but there were signs of hesitation. A month before their wedding, they were seen looking troubled during a bike ride in NYC. Justin later confessed that those tears were about the enormity of getting married, knowing it wouldn’t always be smooth sailing.
Some folks thought maybe they were rushing into things. They had only reconnected three months before they decided to say “I do” at a New York courthouse in September 2018. And then, right after the wedding, Justin was seen crying in the car with Hailey. Some wondered if the wedding night didn’t go as planned.
But insiders said Justin was really serious about staying faithful to Hailey, even going to extremes to make it happen. It showed just how committed he was to making their relationship work.
He went the extra mile by enlisting a close friend from church to serve as a moral guide, helping him steer clear of any temptations. Where does one even find such dependable friends? Maybe through 1-800-WORSHIPPER, 1-800-GOD’S-DISCIPLE, or 1-800-KEEP-YOUR-THING-IN-YOUR-PANTS. Just kidding, but seriously, where do you find such gems? Asking for a friend, of course. The early days of marriage were, well, quite the whirlwind. They openly admitted that adjusting to living together was a real challenge, especially when it came to communication. Hailey was honest about feeling incredibly lonely and missing home deeply. Meanwhile, Justin took to Instagram to share his struggles with his mental health, revealing how tough it was for him to even get out of bed some mornings. He spoke about grappling with anxiety, often seeing the world through a pessimistic lens and fearing what each new day might bring. Maybe a good read of “The Power of Positive Thinking” could help lift his spirits. In an interview with Apple Music’s Ebro Darden, Justin confessed to having an emotional breakdown after their wedding, admitting he had thought marriage would solve all his problems. Instead, it only seemed to add to his worries, especially given his hefty $300 million fortune. And in a rather unconventional move, Justin skipped the whole prenup discussion altogether. Drama alert. According to a source on The Sun website, their whirlwind romance didn’t leave much time for legal matters like prenuptial agreements.
They tried to get a prenup sorted on their big day, but by then, it seemed like too little, too late. According to L. Magazine, Justin started feeling the weight of his fortune slipping away after they said “I do”. Well, that’s karma for you. Maybe they should’ve skipped the formalities and hit the sheets earlier. Might’ve helped Justin think straight. While they could still work out a postnup, there’s been no word on whether they’ve taken that route. Then, in September 2019, they went through another wedding ceremony in South Carolina, with Hailey describing their first year of marriage as seriously tough. So, what made being married to Justin so hard? Well, according to a source speaking to Radar Online, Justin started acting more like a kid than a grown-up. The insider spilled that instead of stepping up, Justin was busy playing pranks on Hailey and acting like a naughty schoolboy. Someone get this guy a therapist! That’s what happens when you don’t get to be a kid, I guess. He didn’t have the luxury of a normal childhood; he was thrown into the spotlight as a celebrity when he was just a kid. Another insider chimed in, saying, “This marriage is all about Justin’s childish needs, and it’s doomed.” And then there were those photos of him looking totally down in the dumps in public again. A source told Us Weekly that Justin had a lot on his mind and wasn’t feeling himself. Sadly, they seemed to suggest that Justin and Hailey’s marriage was at the root of his problems. They said the whole whirlwind engagement and marriage thing overwhelmed Justin, who was only 24 at the time, and he felt like something was missing. To try and cope, Justin turned to his faith, while Hailey apparently spent her days worrying about him and taking care of everything, which must’ve been a huge weight on her shoulders. And then, in March 2022…
Hailey experienced a minor stroke attributed to PFO, a heart condition typically resolved post-birth. Following a successful procedure to address it, Justin faced a setback, necessitating the postponement of tour dates due to Ramsay Hunt Syndrome, which led to facial paralysis. Throughout their health challenges, they provided mutual support, but insiders hinted at Hailey’s growing frustration with Justin’s behavior. Observers pointed out the apparent mismatch in their public appearances, with Justin’s casual attire, including sweatshirts and Crocs, being seen as disrespectful, particularly during Hailey’s significant events. Despite their matching tattoos and Hailey’s stated commitment to their relationship, concerns remain. Hailey acknowledges the effort required to sustain their bond, emphasizing their friendship. Viewers are encouraged to share their thoughts on these relationship dynamics, reflecting on potential red flags. Thanks for tuning in to R to the R to the G.