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Scott Disick and Kourtney Kardashian were together from 2006 to 2015, and after their split, Keeping Up With the Kardashians fans hoped that the couple would remain friends so that they could co-parent their three kids — Mason, Penelope, and Reign. In a Sept. 2016 Instagram post, Scott confirmed that they were on good terms. “Bff goals,” he wrote alongside a paparazzi photo of him and his ex. Sure, it wasn’t exactly a romantic caption, but it proved there were no hard feelings.
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Things got rocky when Kourtney started dating model Younes Bendjima in 2016. And in an Oct. 2017 episode of KUWTK, it became clear how not OK Scott was with that relationship. According to Kourtney, when Scott found out his ex was going on a trip to Cannes with her new boyfriend, he totally freaked out. “We got into like, a full war,” Kourtney told her sisters at the time. Later, he wouldn’t answer Khloé Kardashian’s calls and said he felt that Kourtney was being condescending.
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Scott, who was also in Cannes at the time, was photographed with multiple women — including stylist Chloe Bartoli, Bella Thorne, and Sofia Richie (who he went on to date for three years). But his string of romantic flings wasn’t something he was proud of. “I didn’t see the show, because I was living it,” Scott said in a Nov. 2017 episode of KUWTK. “But look at it [from] my perspective: She was on vacation with one man, a whole trip. That looks like a happier scenario than me, jumping around trying to find happiness and these girls are not fulfilling that. I’m just not happy with anybody.”
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Despite Kourtney’s relationship with Younes, Scott still believed they would ultimately end up together. In a 2018 episode of KUWTK, the Talentless founder told Khloé that he and Kourtney were always planning on reuniting. “We always said we would try to get back together when we were like 40,” he said.
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In that same episode, Scott confessed to Kim that he was feeling “insecure” about the possibility that Kourtney might move on without him. “Like, if Kourtney met someone, fell in love and got married and then everyone’s like, ‘Eh, we have a new Scott — we don’t really need to be close with him anymore,’” he said. “Even though I get it — we have kids [together]. But it’s a scary thing for me.”
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Eventually, Kourtney, Scott, and Sofia got to a point where they could all vacation together with the kids. However, their joint trip to Finland wasn’t without awkwardness. “Sometimes you have so many inside jokes or inside things with somebody you’ve known for so long, even if you’re not romantically with them, you don’t really know how to act,” Scott said in a 2019 episode of KUWTK. “It is definitely a really hard and awkward situation, and I just feel bad. At the end, I want the people I love in my life to be happy.” Did he just say the people he loves?
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In August 2020, Kourtney and Scott shippers thought they found irrefutable evidence that things were heating up between the two. It all started when the Poosh founder shared a photo of herself in a silver swimsuit on Instagram. “lake ya,” she captioned the picture. Then, Scott slid into the comments. “What a lake er,” he wrote. This flirty exchange came just two months after Kourtney shared an image of herself wearing an oversized flannel. “Cute shirt,” Scott commented. Was it his?
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Just because Kourtney and Scott are no longer together doesn’t mean they haven’t discussed potentially having more kids. During the Season 19 finale of KUWTK, fans learned that the former pair joked in a group text about “going for baby number 4.” Unfortunately, Kim couldn’t tell if they were serious or not. “Was that a joke or is that serious?” she asked. “I want to know.” Kourtney then confirmed that, no, they weren’t considering having another child.
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In honor of Mason and Reign’s shared birthday, Scott took to Instagram on Dec. 14, 2020, to celebrate the woman who brought them into this world. “Thank you @kourtneykardash for being the best baby maker in town,” he wrote. “I couldn’t have asked for a better person in the world to have these amazing children with, I love u and our family more than anything in the world.”