Time to Relive Justin Bieber's Complete(ly) Chaotic Dating History

Time to Relive Justin Bieber's Complete(ly) Chaotic Dating History

Hello and welcome to Justin Bieber's dating history—a trip down memory lane that's simply not for the faint of pop culture heart. Before you dive in, please make sure to carve out at least an hour of your day because this list is "It's Been 84 Years"-levels of long, not to mention full of alleged chaos. Like, the Jelena era? The random Kourtney Kardashian hookup? Justin dated quite a bit before settling down with Hailey Bieber, and the time has come to begrudgingly relive the memories.

Caitlin Beadles: ~2018

Meet Justin's very first girlfriend, aka the woman who inspired his song "Never Let You Go."

Alas, they weren't meant to be. Justin and Caitlin split because of Justin's intense touring schedule, but they stayed close and Caitlin (plus her brother) even attended his wedding to Hailey Bieber!

Selena Gomez: December 2009 - April 2014 (on/off)

Rumors of Selena and Justin's epic celebrity romance first started when Justin serenaded Sel with “One Less Lonely Girl” during Dick Clark's New Year's Rockin' Eve. In case you feel like watching that for some unknown reason, here ya go:

These two spent the next few years in what can only be described as an on-again/off-again relationship, which Sel's friends didn't seem to be huge fans of. Like, at one point Taylor Swift was caught on camera making this face at them kissing:

Anyway, Justin and Selena broke up "for good" (this time around) after getting into an alleged fight at Coachella because apparently Selena found photos of Kylie Jenner on Justin’s phone? This is simply speculation by tabloids because Justin and Kylie were never actually confirmed to be a thing, so moving on.

Miranda Kerr: 2012 (rumor)

2012 victoria's secret fashion show runway
Jamie McCarthy - Getty Images

We're (for the most part) not including rumors on this list—it's already long enough as it is!—but Miranda Kerr gets an exception due to the drama of the speculation. There were claims these two hooked up after the 2012 Victoria Secret Fashion Show, but during that time, Miranda was still with Orlando Bloom. The allegation was so dramatic that Miranda's attorney released a statement calling it "false and defamatory."

More importantly, Orlando reportedly tried to punch Justin years later in 2014 while the Biebs shouted "What's up, bitch?"

Chantel Jeffries: January 2014 - February 2014 (~ish)

Chantel and Justin have a somewhat awk history—by which we mean they were reportedly together when Justin was arrested for a DUI while driving a rented Lamborghini. Anyway. Here's a hilarious pic of them in Vegas!

diddy hosts deleon tequila launch party at vanquish
Prince Williams - Getty Images

Yovanna Ventura: March 2014 - April 2014 (~ish)

These two dated in spring 2014 after Justin "noticed" Yovanna on Instagram. "Justin wanted to meet her," a source told E! News at the time. "He sought her out. It hasn't been too hot and heavy, but they have been hanging out a lot. Their relationship is blossoming. I wouldn't be surprised if they have now started dating. He reached out and they started talking in late March. In early April, when he came to Miami they hung out together for that weekend while he was recording in the studio. It was for a couple of days, the weekend. They were getting to know each other."

Cool, here's an incredible photo from this time in our nation's history:

Selena Gomez: June 2014 - October 2014

Sel and Justin got back together in June 2014 and posted the below pic, which Justin captioned (with absolutely no chill): “Our love is Unconditional.”

a person with the head in the hands

But these two once again broke up in October, and the Daily Mail reported that Justin’s “secret liaisons” with Kendall Jenner were the reason behind the breakup. Which brings us to....

Kendall Jenner: October 2014 (rumor)

At least if the aforementioned "secret liaisons" are to believed. But for what it's worth, Justin did confirm to Billboard that he and Kendall dated at some point, telling the outlet it was "never serious" with her.

kendall jenner and justin bieber sighting in paris
Marc Piasecki - Getty Images

Alyssa Arce: August 2014

Alyssa and Justin were spotted making out on a yacht in Ibiza, but sources told TMZ they were "just having fun." Next!

Ashley Moore: March 2015

These two (+ Justin's enormous hat) were spotted at a Clippers game being all sorts of cuddly back in 2015, which naturally lead to dating rumors:

celebrities at the los angeles clippers game
Noel Vasquez - Getty Images

Nothing really came of it, but for what it's worth they were also spotted on a "flirty hike"in 2017.

Shanina Shaik: May 2015

Justin and Shanina were first linked in 2014 when he posted this Instagram—but as you can see, the caption implies they were simply friends.

They reignited dating rumors in May 2015 though thanks to a casual trip to Vegas together:

It's unclear how long they were a thing, but it did not seem super serious!

Jayde Pierce: October 2015 (on/off)

Are a reminder: Jayde was with the Biebs when his nudes went viral in Bora Bora. “He doesn’t let his fame get in the way of doing things," she told to The Mirror re: their vibes. “People think Justin must be a brat and arrogant but he’s nothing like that. He’s a really tactile guy, he loves cuddles.”

Kourtney Kardashian: September - December 2015 (~ish)

2015 mtv video music awards arrivals
Gregg DeGuire - Getty Images

Justin and Kourtney allegedly (and somewhat randomly) hooked up for several months after her split from Scott Disick, and a source told Us Weekly that Justin "bragged" about it.

Hailey Bieber: December 2015 - early 2016

While rumors about Hailey and Justin first started in 2014 after they were seen on a romantic dinner at Mr. Chow in New York, they went official in December 2015 during a cute vacation. (Justin still has the pics up on his IG!)

Anyway, they broke up because apparently Justin was jealous of Drake? As a source put it to People, “Bieber wasn’t happy about [her friendship with Drake] and so they haven’t really been in touch in a bit."

Nicola Peltz: June 2016

saint laurent at the palladium arrivals
Jon Kopaloff - Getty Images

According to Us Weekly, these two briefly dated and a source even said "all his friends love her."

Chantel Jeffries (again): July 2016

nickelodeon's 2016 kids' choice awards arrivals
David Livingston - Getty Images

Justin and Chantel got together again in July 2016, when a source told E! News, "Bieber likes Chantel. He thinks she is a great girl. Chantel would really date Bieber exclusively if he was ready. They have been good friends for a while."

Sofia Richie: early August 2016

Sofia and Justin getting together was a whole thing, mostly because of Jelena fans spiraling and Sel, um, leaving this comment on their picture:


Sofia later told Billboard that her relationship with Justin was “special” and he was “very easy to talk to and that’s hard to find with people in Los Angeles.”

Bronte Blampied: late August 2016

Bronte was rumored to be dating Justin when she joined him on a Hawaiian vacation in fall 2016, and they were also seen out and about in London. Here they are at the airport if you demand evidence:

london celebrity sightings august 21, 2016
Ricky Vigil M - Getty Images

Paola Paulin: early October 2017

premiere of momentum
Matt Winkelmeyer - Getty Images

Justin and Paola dated super briefly right before he got back together with Selena, and a source told Us Weekly that “They’re totally smitten with each other.”

Selena Gomez: late October 2017 - March 2018

Justin and Selena reunited right after Selena’s breakup with The Weeknd, and before long they were taking public bike rides, going on cute walks, and enjoying in kissing sessions at hockey games.

But they broke up for good in March 2018, and neither of them have looked back since.

Baskin Champion: March 2018

celebrity sightings in los angeles june 20, 2018
Nikos/Bauer-Griffin - Getty Images

Justin rebounded from Sel with Baskin, though honestly they were only spotted on *one* date.

Hailey Bieber: 2018 - Now!

Justin and Hailey got back together in summer 2018, when a source told E! News that they “love to party and they love their church organization.” Their relationship was a true whirlwind, and before long they were engaged/married. These days, they're pretty much best described as adorable.

Check out their full timeline below!

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