Disick dated Kourtney Kardashian on and off for nearly a decade before the duo called it quits in 2015. The former couple welcomed sons Mason and Reign in December 2009 and December 2014, respectively, along with daughter Penelope in July 2012. Despite their ups and downs, the reality stars have made an effort to remain friendly for the sake of their little ones.
“The truth is, my problems shouldn’t affect the kids,” Disick exclusively told Us Weekly in June 2019. “Just because their mother and I couldn’t make it as a perfect, romantic couple shouldn’t have anything to do with the kids. They don’t deserve our mistakes, so we figured out a way. We still need to be as honest and as good to each other as if we were together. Let’s raise these children together and that’s it.”
Two months later, Kardashian gushed that she felt “so proud” of how hard she and her ex worked to stay friends. “The hardest part was when we both started new relationships,” she said during a YouTube vlog with Disick in August 2019. “That caused fights between you and I about introducing the kids. We literally had to go to therapy to be able to, like, communicate together.”
Disick chimed in at the time, “The biggest challenge was just trying to figure out how we separate our relationship as friends and parents and still be on the same page.”
Though they initially seemed successful in making that separation clear, the duo’s dynamic took a turn when Kardashian moved on with Barker. Us confirmed in January 2021 that the Poosh founder sparked a romance with the Blink-182 drummer, and he proposed that October.
“He knew it was possible, but is very jealous of Kourtney and Travis’ relationship,” the source exclusively told Us of the Flip It Like Disick alum following the engagement. “Scott still thinks that they could call things off before the wedding.”
Tension continued to grow between the men in August 2021 after Disick sent a DM to Kardashian’s ex Younes Bendjima dissing the former E! personality’s PDA with Barker. During an April 2022 episode of Hulu’s The Kardashians, the lifestyle guru told Khloé Kardashian and Kim Kardashian how she reacted to Disick’s message.
“I wrote him, ‘This is despicable,'” Kourtney said, noting that her former flame apologized via text. “Your actions need to match up with you wanting to be a part of this and act like it. I was in Italy and he was DMing Younes. Then I was like, ‘That’s not really the vibe. Don’t go DMing my ex-boyfriend.'”
Kourtney and the Box Car Racer founder held a small, unofficial wedding ceremony in Las Vegas in April 2022 — but a source previously told Us Disick may “want to stay far away” from the main event.
“It would definitely be awkward if Scott was at the wedding,” the insider revealed in March 2022. “If it’s filmed for sure, then he might there.”
Scroll down to see everything Disick and Barker have said about each other: