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Justin Bieber has been linked to nearly all of the Kardashian-Jenner sisters at some point, but there is the most evidence that he actually dated – or at least had a fling with – both Kourtney Kardashian and Kendall Jenner. It also seems like their romances weren’t very far apart. Here’s what we know about the Justin Bieber, Kourtney Kardashian, and Kendall Jenner love triangle. 

Side by side photos of Kourtney Kardashian, Justin Bieber, and Kendall Jenner, who were once in a love triangle.
(L-R) Kourtney Kardashian, Justin Bieber, and Kendall Jenner | David Crotty/Patrick McMullan via Getty Images; Dimitrios Kambouris/Getty Images; Mike Coppola/Getty Images

Justin Bieber and Kourtney Kardashian rumors started after the 2 stars were spotted together at a restaurant 

Rumors that Justin Bieber and Kourtney Kardashian were dating started around October 2015. They were spotted together at The Nice Guy in West Hollywood, where they arrived separately but left together in Bieber’s black Escalade. 

Kardashian and Bieber then headed to Universal Studios Hollywood Horror Nights, accompanied by a few other people. An onlooker told ET that the “Sorry” singer “was walking with his arm around Kardashian and joking with her about being scared.” Bieber even shared a black and white photo of the two on Instagram. 

The two were spotted together several more times, including in December 2015, when ET reported that Bieber and Kardashian were “nearly inseparable” at The Nice Guy again. 

In a Dec. 17 interview with The Bert Show, Bieber opened up about the rumors he was dating the reality star. “I’m being used, man. What can I say?” Bieber joked (per People). When host Bert Weiss asked, “Anything there?” Bieber responded, “Nah, we’ll leave it at that.”

He added, “No, no, but for real, she’s great. I’ve known [the family] for years.”

Hailey Bieber reportedly has a rule that Justin Bieber can’t hang out with Kourtney Kardashian

A recent article has contributed to the suspicions that Justin Bieber and Kourtney Kardashian were more than family friends. 

In an article titled, “8 Strict Rules Justin And Hailey Bieber Make Each Other Follow To Maintain A Strong Marriage,” the publication claims that rule number four in the Biebers’ marriage is that the “Peaches” singer can’t hang out with Kourtney Kardashian. 

Hailey allegedly created the rule after getting engaged to Justin in 2018, following Kardashian’s split from her then-boyfriend, model Younes Bendjima. 

Justin and Hailey officially dated for the first time in 2016, not long after the rumors that he had been hooking up with Kardashian. 

“Hailey has every reason to feel threatened,” a source told Hollywood Life in August 2018. “Now that she’s [Kourtney] single, she’d go after Justin again in a heartbeat.”


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There were rumors that the singer also hooked up with Kendall Jenner

Kourtney Kardashian isn’t the only member of her famous family that Justin Bieber is rumored to have hooked up with. There has also been speculation that the “Stay” singer had a fling with Kardashian’s younger half-sister, Kendall Jenner. 

The rumors started after Bieber and Jenner provocatively posed together for Vogue in March 2015. They looked like a gorgeous couple in the photos, and they had been spotted spending a lot of time together, leading fans to believe they were an item. 

In a November 2015 interview with Billboard, the reporter wrote that Bieber said “it was never serious with Kendall Jenner.” Even though it was never serious, it sounds like the two stars had some sort of relationship beyond friendship. 

But Jenner denied the rumors during an appearance on Nightline. “He’s a longtime friend of our family,” the Keeping Up With the Kardashians star said (via E! News). “Everybody loves to assume things, but no.”

In recent years, Jenner and her boyfriend, Devin Booker, have double-dated with Justin and Hailey Bieber. So, whatever relationship Jenner had with the pop star, it wasn’t enough for his wife to ban him from hanging out with her, like she reportedly has regarding Kardashian.