Strange Things About Justin Bieber And Hailey Baldwin's Relationship

Well, that escalated quickly. After just a month of over-the-top, coast-to-coast PDA, Justin Bieber proposed to Hailey Baldwin while on vacation in the Bahamas in July 2018 — and she said yes. A source told TMZ that Bieber got down on one knee in Baker's Bay in front of a crowd, but only after his entourage made everyone nearby put their phones away.

An insider told E! News, "Justin made arrangements for the ring when they were in New York City 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." The source added, "The proposal was a very happy moment and Hailey was taken off guard. Her face was in shock but you could tell they are both so in love." The insider added that while Bieber and Baldwin had previously discussed marriage, the model had no clue it would come up so seriously so soon. That said, TMZ cameras caught the pair with matching gold rings on their all-important fingers in June 2018, so it's not like they really worked to quell speculation before tying the knot that September.

Their quickie engagement isn't the only bizarre thing about the couple known as "Jailey." Here are the strangest things about Justin Bieber and Hailey Baldwin's relationship.

Justin Bieber previously hooked up with her friends

Remember how the Spice Girls said "If you wanna be my lover, you gotta get with my friends?" And remember how weird that seemed to most of us because of the whole "rules of feminism" thing? Well, apparently it's not too weird for Baldwin, because Bieber was once rumored to have gotten hot and heavy with quite a few of her pals ... and they're all related. Creepy.

People reported that Bieber had been hooking up with Kourtney Kardashian in December 2015, with a source dishing that it was a "deep flirtation" that lasted months but was never serious. "Kourtney is great. Justin thinks it's cool that she is older and hot," a source told People. "She isn't clingy and has her own life. There are no bad consequences for Justin to hook up with her. She is very easy going and just makes it fun for him to be around her."

Bieber was also previously linked to both Kendall and Kylie Jenner, but neither gal apparently took issue with him hooking up with their much older sister ... so maybe that's why Baldwin was seemingly fine with him fooling around with her BFFs. Heck, maybe it's just a sign that he was previously vetted and approved.

Hailey Baldwin hooked up with one of his pals

Hailey Baldwin was linked to Drake, a fellow Canadian and casual pal of Bieber, in May 2016. People reported that Drizzy and Baldwin got cozy at a Memorial Day party together, with a spy saying the pair "were having a lot of fun together and were very affectionate." An insider later told the magazine, "Drake and Hailey are dating super casually, but he is really into her. They met through mutual friends and are taking things slow."

Insiders told Us Weekly that while the rapper was smitten with Baldwin, she was still too hung up on Justin Bieber at the time to return any of his affections. What's more, an insider insinuated to E! News that while Baldwin was gallivanting around with the Toronto-born MC, she was still pining for Bieber and upset that her ex was hooking up with actress Nicola Peltz. "[Hailey] always has been such a good friend to [Bieber] and she feels disrespected by many things he has done lately," the source said at the time. "...Hailey wants to be with Justin but he is just always back and forth with her and that drives her mad."

Bieber once ditched her for an ex at his birthday party

It's his party, he can cry... or hook up with... whoever he wants to, and if the rumors are true, that's just what he did. When Bieber celebrated his 21st birthday in March 2015, Baldwin was on hand to mark the special occasion with him. So was his former fling, Yovanna Ventura. Bieber was reportedly all over Ventura right in Baldwin's face, so she ended up bailing on the festivities earlier than expected.

A source told Hollywood Life, "She says she's cool with him being with other girls, but putting it in her face like that was too much ... She didn't throw a big fit, she didn't pick a fight with Yovanna, she just left. She was supposed to stay until the end of the week but she bounced early."

Baldwin posted some cryptic tweets following her departure: "I just gotta do my own thing sometimes." When a follower asked if she left because Bieber was "being a jerk," Baldwin replied, "I didn't have to leave for that, I left because I wanted to." Did you notice that she didn't deny the "jerk" part? Yes, we caught that too.

Did Bieber initially use Baldwin to make Selena Gomez jealous?

Hailey Baldwin was rumored to be Justin Bieber's rebound for years during his off-again phases with his first love, Selena Gomez. He seemed to treat both ladies so poorly — often concurrently — that it really took a toll on all three points in this high-profile love triangle.

In December 2017, sources close to Bieber told TMZ that, while briefly reconciling with Gomez, he reportedly reached out to Baldwin to apologize to her for mistreating her and breaking her heart in the past. Their contact was supposedly purely in the spirit of Bieber making amends in an effort to live more openly and honestly within the Hillsong Church, but it allegedly triggered Gomez to flip out. After Bieber and Gomez split for the umpteenth time in March 2018 (despite People reporting that April that he was still in love with Gomez and wanted her back), the Biebs began stepping out with Baldwin again. Considering the "Sorry" crooner married Baldwin just months later, it seems as though he'd already moved on from the "Back to You" singer by the time "Jailey" rekindled their romance.

Jailey beefed during his fling with Sofia Richie

Oh, you thought the Yovanna Ventura incident was the only time Bieber played Baldwin to her face? The rumor mill claimed he did her dirty at least one other time — with brief fling Sofia Richie.

Sources told People in August 2016 that though Bieber and Baldwin were never "officially a couple," those in their circle "knew they were together." Perhaps it was common knowledge, but Bieber was also supposedly hooking up with a different blonde celebrity spawn: Sofia Richie. Richie reportedly urged Bieber to unfollow Baldwin on social media, because, well, one could argue that no one involved in this situation was a fully-functioning adult. "Justin unfollowed Hailey on social media, and now all their friends are talking s**t on Sofia and him and how messed up it is," a source said.

Baldwin didn't directly address the drama, but she post some interesting thoughts on Instagram: "We've all had our fair share of things we've done, both good and bad. What makes the present so powerful is when we take complete responsibility for our actions, we allow ourselves self-growth. Misplacing the blame onto someone else isn't going to get you to the next stage in life, so try not to manipulate a situation to make yourself look better. The truth always come to light, so it's better just to own it."

Or, you know, just stop it with the Instagram hate and grow up. Tomato, tomahto.

Bieber didn't want to settle down with Baldwin for a very long time

Justin Bieber told GQ in February 2016 that he and Baldwin weren't in a relationship — a fact he seemed to emphasize as much as possible, conceding only that they were friends who kissed. Fair enough. He also revealed why he refused to commit at the time.

"I don't want to put anyone in a position where they feel like I'm only theirs, only to be hurt in the end. Right now in my life, I don't want to be held down by anything. I already have a lot that I have to commit to. A lot of responsibilities. I don't want to feel like the girl I love is an added responsibility," Bieber said. "I know that in the past I've hurt people and said things that I didn't mean to make them happy in the moment. So now I'm just more so looking at the future, making sure I'm not damaging them. 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."

While Bieber didn't want to hurt Baldwin, we also suspect he did want the freedom to hook up with other people. Thankfully, it seems he's since truly turned a corner.

They don't have a lot of practice with exclusivity

Hailey Baldwin and Justin Bieber were off and on for a long time, but reportedly just as friends with benefits — something he made clear and something she seemed to be okay with, because she said as much herself when they were packing on the PDA in early 2016.

"We are not an exclusive couple. He's about to go on tour," she told E! News at the time. "Relationships at this age are already complicated, but I don't really like to talk about it because it's between me and him." Baldwin added, "I live a very public life and I have to keep things personal or else I have no personal life. It's very difficult. I am very open on social media, but that's why I don't like to talk about certain things ... and I like to think my relationships are not between me the person and the whole entire world. It's hard. I don't think people are really able to understand if they're not in that position."

We're trying, Hailey. We're trying.

Bieber and Baldwin stopped speaking for a very long time

Baldwin admitted that because of the drama associated with her messy on-again-off-again-not-really-official relationship with Bieber, they stopped talking for nearly a year in the past.

"Justin and I were friends for a long time. I met him when I was really young and he was one of my best friends," she told The Sunday Times in May 2018. "Everybody knows that at a certain point in time that turned into something else, but that just happens when you're 18, 19. It was what it was." She added, "We went through a long period when we weren't friends," but have "moved past that" and learned from their "high-profile relationship." 

"It brought both of us to the realization that we just work much better as friends," Baldwin continued at the time. "He's somebody I really cherish. Now it's a very mature situation. It's good." Of course, "good" may have been an understatement. Apparently, their rekindled relationship become downright fantastic in just a matter of months.

Baldwin was close with Shawn Mendes until right before their engagement

Less than two months before she and Bieber got engaged, Baldwin had tongues wagging when she walked the red carpet at the 2018 Met Gala with Shawn Mendes. Though the pair insisted they weren't dating, their slew of social media posts together, as well as what seemed like a red carpet couple debut, led to a lot of speculation that they were a couple.

"No, we were not making our debut," Mendes told People after fashion's biggest night. "Obviously Hailey and I are friends, and it was just really cool for me to be able to walk with her because she's a vet and it was my first year, so it kind of took the pressure off a little bit. I was thrilled to be able to go with her."

People also thought these two were an item because they were spotted holding hands at a Halloween party in 2017 and appeared to get cozy over the holidays, but when Baldwin wiped her Instagram clean of Mendes after getting together with Bieber in June 2018, it really blew the internet's mind — and maybe Mendes'. When asked if Baldwin and Bieber were an item at the time, Mendes quipped to Canada's ETalk, "I don't know if they're dating or not. I love them both."

Justin Bieber almost went to jail for hanging out with Hailey Baldwin

Though Bieber is reportedly in a good place these days, he almost faced a warrant for skipping out on his responsibilities in June 2018 to pucker up with Baldwin in the Big Apple.

TMZ reported that Bieber's former neighbor, Jeffrey Schwartz, requested a warrant be put out for Bieber's arrest for skipping a deposition in Schwartz's lawsuit against the singer. The lawsuit involved Bieber allegedly egging Schwartz's Calabasas, Calif. home and verbally harassing him. Though Bieber was already criminally charged for incident — and paid a cool $80,000 in restitution in the case — Schwartz sued Bieber in civil court for emotional distress and pain and suffering as the result of living next door to the Biebs. Bieber reportedly had a deposition in the suit slated for June 22, 2018, but missed it, leading Schwartz's legal team to demand that the singer pay $1,000 for every day he didn't sit for questioning, as well as face jail time for his alleged negligence of his responsibilities in the case.

While Bieber's legal team later told TMZ that the singer's attorneys provided alternate dates to sit for the deposition, Schwartz's lawyers supposedly went right to a judge to ask for a warrant instead of attempting to reschedule.

Hailey Baldwin was obsessed with 'Jelena'

Years before Baldwin and Bieber got together, the model was simply a fangirl, not just of Bieber, but of Selena Gomez, often tweeting about her obsession with them as a couple. That's got to be a little awkward for them to look back on now, no?

"I don't care what anyone says but Justin Bieber and Selena Gomez together is the definition of a teenage dream! #word," a 14-year-old Baldwin tweeted (via The Sun) in 2011. The same year, she tweeted that she needed wrapping paper of the singer "ASAP." In 2012, after the Academy Awards, Baldwin quipped: "I gotta say I was really looking forward to seeing what color coordination Jelena was gonna do for this years VF party.. #sigh #ohwell." 

A deep dive into Baldwin's Twitter history reveals that she has also called Gomez "beyond flawless" and declared herself "100 percent team Jelena" in the past. Baldwin was even photographed clutching a copy of M magazine with Jelena on the cover and this headline: "Why Selena knows she won't marry Justin." Whoa.

Her dad played a pivotal role in their relationship

Hailey Baldwin's father, actor Stephen Baldwin, may well be the reason Bieber and Hailey got engaged in the first place.

Fans on Twitter dredged up a video from 2009 of Stephen introducing Hailey to Bieber, telling the then-bowlcut tween, "We've been enjoying your music." Bieber actually commented on the clip, calling it "amazing" in January 2016 (when he and Hailey were in an on-again phase.)

Around that time, Stephen told TMZ that he "absolutely" approved of Bieber dating Hailey, but added, "There's no label on it ... just friends. Mr. Bieber is a wonderful young man, hugely talented, has a whole lot of success ahead of him." When asked if Bieber would have to ask his permission to marry Hailey, Stephen giggled, "We're far away from that."

But it turns out Biebs did, in fact, ask Stephen for his daughter's hand. Sources told Entertainment Tonight in July 2018 that the singer reached out to Stephen weeks before popping the question. "Justin and Stephen have always had a close relationship, and Justin wanted to show his future father-in-law how serious he is about his future with Hailey," an insider claimed, adding that Stephen and Bieber discussed "relationships, sacrifice and religion" before papa Baldwin gave his blessing.

What does Selena Gomez think of all this?

The whole world was wondering what Selena Gomez thought of the Bieber-Baldwin engagement news, but it seemed like, well ... not much at all. A source that sounded suspiciously like someone who may be in Gomez's camp told E! News in July 2018, "Selena knows that Justin makes rash decisions, but wishes them both the best. She is truly focused on herself and Justin is no longer a topic of conversation in her life."

Around that time, an insider told Radar Online that Bieber had been texting Gomez for months, but she supposedly didn't respond because she "really has nothing to say to him." The source added, "At first, Selena didn't believe the news. She is not devastated by any means. She was the one to end it once and for all with him ... She thinks the whole thing is a joke and knows it will never last." Ouch! Gomez was later spotted rocking a T-shirt that read, "Only the strong survive," which may or not have been in reference to the ring news. 

As of this writing, Gomez has yet to publicly comment on her ex's marriage. However, an insider cited by In Touch Weekly in February 2019 claimed, "She's sent Justin very loving messages of support [and is] wishing Justin the best."

Justin Bieber might still have a Selena Gomez tattoo

Well, this must have made hugs awkward: Despite Bieber later tying the knot with Baldwin, he was still boasting a tattoo of Gomez, stylized to look like an angel, on his forearm when these two got engaged. However, a source told The Sun, "Justin's already got plans to get rid of the tattoo. He's tried to get it partially covered up before, but this time he's determined to get rid of it for good. He's going to his regular tattoo artist, Bang Bang, to get something inked over the top. I think he wants it gone in time for the wedding to Hailey."

While it's remained unclear whether Bieber went this route, he previously addressed his ill-thought out ink, telling GQ in 2016, "This is my ex-girlfriend, I kinda tried to cover her face up with some shading, but people still know."

Despite the drama, Bieber insisted in April 2018 that he loved all of his body art, writing on Instagram, "If tattoos didn't hurt everyone would have them ... Over a hundred hours of [art] work on my body and I wouldn't take back a single one ... I've made my body a canvas."

Even John Mayer thought their PDA was ridiculous

Shortly after the engagement news went public, Bieber posted a PDA-filled Instagram snap with Baldwin. In the photo, the couple is making out in a hot tub, but who took this picture? Bieber's hands are around Baldwin's neck, and her arms are wrapped around his waist. This mystery wasn't lost on notorious Lothario John Mayer, who took it upon himself to comment on the captionless post. Mayer's missive was captured on the popular Instagram account known as "Comments By Celebs."

"Interesting dynamic with the photographer in the hot tub," Mayer wrote. "That's gotta feel super third wheel. I see a lot of myself in this hot tub photographer. Imagine being in a hot tub on business." You know things are bad when the guy who blabbered about "sexual napalm" calls you out for oversharing your romantic exploits. Take it down a notch, kids.

Jailey allegedly wed on a whim

Justin Bieber and Hailey Baldwin's whirlwind engagement ended in what appeared to be a whirlwind wedding. A source cited by People on Sept. 14, 2018, about two months after the couple got engaged, claimed they'd secretly tied the knot "without telling anyone."

The day before the marriage report, TMZ obtained photos of Baldwin and Bieber at a New York City courthouse that provides marriage licenses. There, Bieber reportedly thanked a court official for "keeping it on the DL," though he didn't specify what "it" was. A witness claimed he was crying and telling Baldwin, "I can't wait to marry you, baby."

According to TMZ, the pair were already planning to host another ceremony and party in front of family and friends, possibly at an estate Bieber purchased in Ontario, Canada. An insider claimed, "They're going to have a blowout in front of God and everyone they love." While the married pair have since kept much of their wedding planning to themselves, People reported in June 2019 that Jailey apparently planned to follow their courthouse wedding up with a second ceremony held on their first anniversary. According to an insider, "They are both excited."

Hailey Baldwin may have been in a hurry

Just days before reports surfaced that Bieber and Baldwin had wed, she made it clear in an interview with The Cut that she wasn't getting any younger. "My sister was 24 when she got married, and my parents also go married when they were young too," she said. "I see no reason to wait. When you know it's right, it's right."

The model added that those close to her would likely have intervened if they weren't true Beliebers. "I said to them, 'You'd stop me if you didn't think this was the right decision, right?'" Baldwin explained. "And they didn't."

It's important to point out that one of the more obvious reasons for rushing to the altar didn't necessarily apply to Jailey. Sources told TMZ in September 2018 that this was not a shotgun wedding, insisting that Baldwin was "100 percent not pregnant."

A marriage certificate didn't mean much to these two

Despite reportedly getting their legal ducks in a row at the courthouse, Bieber and Baldwin are said to not believe they're legitimately married because no religious ceremony was performed ... yet. 

After reports emerged that she and Bieber tied the knot, Baldwin tweeted (via Entertainment Tonight), "I understand where the speculation is coming from, but I'm not married yet!" The tweet has since been deleted. Scandal! Meanwhile, a source told People that Baldwin's denial was because she "feels a civil ceremony and their 'real' wedding are two separate things." A religious insider added, "What happened at the courthouse is a courthouse thing — a legal thing. But marriage is two people making a vow before God and the people they love."

When The Blast caught up with Bieber and Baldwin in the Big Apple and asked about the wedding, Bieber didn't respond and merely looked really irritated at the question. The site also reported that they obtained a marriage license so they could actually have a ceremony and party "whenever [Bieber] wants" — which, as pointed out above, would likely happen in September 2019.

Baldwin watched Bieber's life hit 'a pretty dark' period

Justin Bieber revealed he was going through a tough time during his truncated Purpose tour in 2017. Since then, he's come clean about everything he was dealing with in the years leading up to that time.

"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," Bieber told Vogue in February 2019. "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. Drugs put a screen between me and what I was doing. It got pretty dark. I think there were times when my security was coming in late at night to check my pulse and see if I was still breathing."

Bieber retreated with Hillsong Church pastor Carl Lentz in N.J. to recover. While he's clean from drugs, he said he still "drinks alcohol socially." According to his new wife, Bieber's never actually be in a rehab program. Of the dark times, Hailey Baldwin said, "I grieved very intensely over the whole situation. I just wanted him to be happy and be good and be safe and feel joy. But I'm really proud of him. To do it without a program, and to stick with it without a sober coach or AA or classes — I think it's extraordinary. He is, in ways, a walking miracle."

Bieber believes she was the 'reward' for his celibacy

Justin Bieber and Hailey Baldwin's marriage seemed like a whirlwind, and there's perhaps one obvious reason they seemingly rushed to the altar: They were saving themselves for marriage.

Bieber admitted he'd been celibate for about a year before marrying Baldwin (which, thanks to Cosmopolitan's quick math, means he was likely celibate while dating Selena Gomez, just months before he broke up with her and seemingly rebounded with Baldwin). The reason? Vogue reported in February 2019 that sex addiction was the one vice Bieber couldn't seem to kick completely, so he tried to go cold turkey as long as he could without bedding any beauties, including his then-future bride. Bieber, unlike Trent Reznor of Nine Inch Nails, reportedly believed that abstinence would bring him "closer to God."

"He doesn't ask us not to have sex for him because he wants rules and stuff. He's like, 'I'm trying to protect you from hurt and pain,'" Bieber said of God. "I think sex can cause a lot of pain. Sometimes people have sex because they don't feel good enough. Because they lack self-worth. Women do that, and guys do that. I wanted to rededicate myself to God in that way because I really felt it was better for the condition of my soul. And I believe that God blessed me with Hailey as a result. There are perks. You get rewarded for good behavior."

Justin Bieber and Hailey Baldwin are already having relationship problems

In Justin Bieber and Hailey Baldwin's joint interview with Vogue in February 2019, Baldwin lamented that marriage is "really effing hard," and Bieber confessed that he has trust issues in general that extend to his new wife. He added, "We've been working through stuff. And it's great, right?" The couple also said living together has been challenging and that they're working on their communication.

"He'll say,'I feel,' and I'll say, 'I think.' I have to really dive deep and struggle to be in touch with my emotions. He gets there immediately," Baldwin explained, while Bieber described himself as "the emotionally unstable one." However, Bieber has looked to Baldwin as a sense of stability, explaining, "I've always wanted security — with my dad being gone sometimes when I was a kid, with being on the road. With the lifestyle I live, everything is so uncertain. I need one thing that's certain. And that is my baby boo."

The music star also noted that they argue often, but allegedly in a healthy way: "Fighting is good. Doesn't the Bible talk about righteous anger? We don't want to lose each other. We don't want to say the wrong thing, and so we've been struggling with not expressing our emotions." His preferred way to express himself is to do it in the moment. But Baldwin? "You'll get it out of me the next morning."