The former couple dated on and off from 2006 to 2015 before finally pulling the plug on their romance and going their separate ways. The Keeping Up With the Kardashians star and the Flip It Like Disick personality each moved on since calling it quits with each other — but their connection has never fully fizzled out. During an August 2019 episode of his reality show, however, Disick admitted that he felt “insecure” while he was dating Kardashian.
“I feel like years ago, when I was, like, younger and stuff, I don’t know that I’ve been, like, motivated to, like, do all these things for the kids and, like, build houses for them,” he told his ex, referring to their sons Mason and Reign, and daughter Penelope. “I was just so insecure that, like, everybody would look at me like I’m not cool or young anymore. And now, I couldn’t be happier.”
Following his emotional split from Kardashian, Disick dated Sofia Richie from September 2017 to May 2020. Shortly after his breakup from the model, an insider told Us Weekly that he and Kardashian still behave “like best friends” and are getting along better than ever.
“Kourtney is not open to him in a romantic sense, but Scott is always flirting with her and thinks she looks better than ever,” the source added at the time. While their relationship might seem “weird to everyone else,” they’ve consistently had each other’s back through all of their ups and downs.
A separate source hinted that Disick’s connection with Kardashian came in between him and Richie before they called it quits. “Scott is always going to be in love with Kourtney, and that’s something Sofia has had to face since even before she got serious with him,” the insider said in May. “It just became more apparent that his family was more of a priority than she was, and his family would be his main priority over anything and anyone.”
While Disick and Richie reunited in July 2020, another insider told Us that his family with Kardashian remained his priority.
Scroll down to look back at all the times Disick and Kardashian flirted on social media since their split.