Justin Bieber recently stirred the internet by posting a picture with Kendall Jenner on his Instagram, and naturally, fans had thoughts. While many of his followers, including wife, Hailey Bieber, left supportive comments on the post, some were confused by the moment of affection between Justin and Kendall, who happens to be one of Hailey’s closest friends. The snap reignited much speculation and curiosity online, with people questioning the nature of Justin’s relationship with the model. But what many may not realise is that Kendall and Justin have been close for years, long before his marriage to Hailey. In fact, their bond is just one chapter in a much longer story.
Justin Bieber’s connection to the Kardashian-Jenner family runs surprisingly deep. From being neighbours with one of them and selling his mansion to another, to having flirty moments with Kylie and even sparking brief dating rumours with Kendall, the pop star has long been entangled in the world of reality TV royalty. He’s been close to the family and a friend for decades now. As Justin Bieber and his picture with Kendall continue to make headlines, here’s a full timeline of his dynamics with each member of the famous family, from friendships to flings and everything in between.
Justin Bieber had called Kim Kardashian his girlfriend
Back in 2010, Justin Bieber and Kim Kardashian sparked a wave of media frenzy after the then-16-year-old pop sensation posted a cheeky photo of the two on Twitter, captioning it “Look, it’s my girlfriend.” The playful tweet sent Beliebers into a frenzy, with many fans reacting so aggressively that Kim later admitted she began receiving death threats from Justin’s loyal followers.
Trying to calm the chaos, Justin clarified the nature of their relationship by tweeting, “Kim is a friend. A very sexy friend but a friend. No need 4 threats”. Despite the intense fan reaction, the exchange between them was lighthearted, and the two even posed together for an Elle magazine shoot later that year, further fueling speculation,. However, both parties maintained it was all in good fun.
While the flirtation between Kim and Justin made headlines, there was never an actual romantic relationship between Kim and Justin, just a moment of friendly teasing that went viral during Justin Bieber’s early superstardom. However, the two have remained friendly, posing together and taking pictures whenever they meet at red carpets or shows.
Justin Bieber and Kourtney Kardashian had a rumoured fling
In late 2015, whispers of a playful fling between Justin Bieber and Kourtney Kardashian made headlines. Kourtney had broken up with her long-term on-and-off boyfriend, Scott Disick, and was seen with Justin multiple times as the two went partying together, including at L.A.’s popular hotspot The Nice Guy.
Their frequent outing fueled speculation about their connection, and the atmosphere became even more charged when Justin shared an Instagram photo captioned “Lord knows,” widely interpreted as a pointed reference to Kourtney’s ex, Scott Disick, who famously calls himself Lord Disick.
By January 2016, outlets like Us Weekly reported the pair were ‘hooking up casually,’ describing the relationship as lighthearted, fun and nothing serious. Despite the buzz, there’s no evidence this was anything more than a brief romantic dalliance. The two never directly addressed this.
Khloe Kardashian bought Justin Bieber’s house
In 2014, Khloe Kardashian bought Justin Bieber’s mansion in Calabasas for USD 7.2 million; she moved into the same exclusive neighbourhood he was leaving behind. He previously had been in the headlines for partying too loudly and for numerous noise complaints being filed against him, which eventually led him to sell the house.
Khloe’s new home also put her close to her sister Kourtney Kardashian, who had just moved nearby and was neighbours with Justin previously. While there was no public connection between Khloe and Justin, the house deal kept them linked in an unexpected way.
Justin Bieber and Kris Jenner know each other through a common friend
Justin Bieber’s familiarity with Kris Jenner isn’t just because of his friendship with her daughter. In fact, there is one more person special to both of them who acts as a common link between them. It’s Corey Gamble, who once served as Justin’s tour manager under Scooter Braun’s SB Projects, BustleCapital.
Corey has been dating Kris for a long time now. In August 2015, Justin publicly called the pair the “hottest couple in the game” when he shared a photo of them from Kylie Jenner’s 18th birthday on Instagram. This social media shout-out showcased how intertwined Justin’s world is with the Kardashian-Jenner orbit.
Justin Bieber, Selena Gomez and Kylie Jenner Drama
In 2014, tensions flared between Justin and Selena when she reportedly discovered flirtatious texts and photos from Kylie Jenner on Justin Bieber’s phone, which allegedly strained their friendship and prompted Selena to unfollow both Kylie and Kendall on Instagram. Despite the drama, Justin and Kylie maintained a close friendship. In an ELLE interview, Kylie explained how Justin has also grown up in the spotlight himself, and often offered her genuine support during hard times.
Reflecting that empathy, Justin publicly defended her in a Billboard interview, saying he wants people to be more kind to young celebrities like Kylie. While many media outlets have time and again linked them together, their connection appears rooted in mutual understanding and camaraderie rather than romance. The two have never addressed any speculations around them and remain close friends.
Justin Bieber and Kendall Jenner have raised many speculations time and again
Justin Bieber and Kendall Jenner’s connection has long teased the tabloids with romantic tension and fashion-forward flair. In September 2014, the duo fueled speculation when they were spotted dining together in Paris. The two were dressed elegantly, driving through the city in a Rolls-Royce, and enjoying what seemed like an intimate evening at Ferdi restaurant.
Months later, the pair took their chemistry to the pages of Vogue, appearing together in the April 2015 issue’s ‘Hollywood’s New Brat Pack’ shoot by Mario Testino, where they exchanged cosy, stylish looks, fanning the flames of romance rumours. Yet, Kendall has consistently downplayed any romantic implications, telling Nightline in November 2014 that Justin was just a longtime friend of her family.
Kendall has time and again insisted that reports of anything more than them being friends should not be taken seriously. Justin added another layer of clarity in a Billboard interview the following year, remarking that their connection ‘was never serious,’ many eagle-eyed fans dissected this as a subtle hint that while something may have existed, it wasn’t deep.
Today, Justin Bieber is happily married to Hailey Bieber, a longtime friend of Kendall Jenner. The two models have been close for years, often seen vacationing together and attending fashion events side by side. Despite past rumours linking Kendall and Justin, the trio maintains a friendly and drama-free dynamic. In fact, Kendall has continued to support the couple publicly, and all three have been spotted hanging out, proving that whatever history may have existed, it’s friendship that’s lasted.
From flirty rumors to friendly ties, Justin Bieber’s long-standing connection with the KarJenner clan proves he’s been part of their inner circle for over a decade. What are your thoughts about Justin Bieber and his dynamics with The Kardashian-Jenner family?
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