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.

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."

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.

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.

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.

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'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.

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."

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."

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.

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."