2. The Time He Allegedly Dated Kourtney Kardashian
Despite the fact that Kourtney Kardashian is significantly older than Justin, the twosome reportedly hit it off right after their first “date” in Hollywood during the Christmas period. Kourtney had just ended things with Scott Disick, so she was single and ready to mingle — but nobody would’ve expected her to hook up with a boy that is so much younger than her. Regardless of their age difference, despite credible reports claiming the two hooked up, Justin refuses to confirm the allegations, making it appear that the romance was a mistake, and perhaps something he wasn’t proud of.
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