Kendall Jenner and Scott Disick have endured quite the ups and downs, though it now appears that things might be at their worst.

HIGHLIGHTS

 Despite rumors and tabloid headlines, Kendall Jenner and Scott Disick have denied ever hooking up, calling the rumors false.
 Kendall Jenner trolled Scott and ex-girlfriend Sofia Richie on social media, but they have since moved past any tension and have been seen hanging out together.
 Kendall and Scott have had their ups and downs, as seen on an episode of “The Kardashians,” but they remain friends and Scott will always have a place in the family as the father of Kourtney Kardashian’s three oldest children.

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Article updated December 2023.

Through the years, Scott Disick, 40, has maintained a relationship with the Kardashian-Jenners even after his breakup from Kourtney Kardashian, 44. At one point, fans also rooted for him to date his ex’s sister, Khloe Kardashian, 39. Wild, right? But not as crazy as the rumors about the Flip It Like Disick star sleeping with Kendall Jenner, 28. Many people actually believed it… After all, Disick has a reputation for dating women her age.

Both Kendall Jenner and Scott Disick have been involved in multiple relationships since the rumors first surfaced, but what’s their relationship is really like?

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Did Scott Disick And Kendall Jenner Ever Hook Up?

During the 10th anniversary special of Keeping Up with the Kardashians, executive producer Ryan Seacrest asked the family about the craziest tabloid rumors about them at the time. The first image that came up was of OK Magazine with the 2017 headline, “Kendall: How Scott Seduced Me!” Kendall laughed it off, saying, “I didn’t even know that existed.” Kris Jenner also chimed in, saying, “That’s hitting the bottom of the barrel.”

Scott also addressed how ridiculous it was given their age gap. “Damn, I had you when you were young,” he said, rather creepily. Kendall responded, “Definitely false.”

That bizarre rumor may have started in 2016. As an April Fools’ prank, Kourtney posted a Snapchat video pretending to catch Kendall and Scott in bed. Then, in March 2022, the rumors were fueled again when Scott posted a photo of Kendall wearing a sports bra and tights. “Posing in a swimsuit at your sisters ex-boyfriends house? No not normal,” said a Redditor.

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Another one said that it might be part of their Hulu show, The Kardashians. “Why do i feel like this is gonna be featured on the Hulu show?” they said. Others also came to Scott’s defense. “Honestly? They’ve all been on beach vacations together,” wrote a commenter. “This is genuinely more clothed than any of their swimsuits. and he’s know her since she was like 11. I don’t blink at my siblings in swimsuits.”

Kendall Jenner Shaded Scott Disick And Sofia Richie’s Relationship

When she was only 19, Sofia dated a then-34-year-old Scott, sparking controversy amongst fans for their big age gap. A few months into their relationship in 2018, Kendall trolled the couple as they posted a photo of them together with Scott and Kourtney’s kids. “Aww Scott and his kids,” the model said in the comments. Fans initially thought that Kendall and Scott were feuding. But not long after her comment, Kendall was spotted skydiving with her ex-brother-in-law.

Kourtney eventually warmed up to Scott’s relationship as well. Despite Lionel Richie calling it “a phase,” a source said that for Kourtney, Sofia was an amazing potential stepmom. “Sofia is helping Scott be a better, healthier person,” said the insider. “Kourtney feels confident that Scott and Sofia takes good care of the kids. Scott is a great dad when he has his life together.” In October 2019, the mom-of-three even joined the lovebirds on a family getaway with the kids.

The three of them were also seen hanging out in a hot tub together during an episode of KUWTK. Of course, viewers thought it was awkward. But for them, it was all casual.

“I never want to miss out on anything when it includes the kids,” Scott said of the odd arrangement. “The past six to eight months, we’ve been on a couple trips where it’s been Kourtney, Sofia, the kids, and it’s been great. But Sofia mentioned to me that she feels a little left out, so I have to be careful not to overstep anyone’s boundaries and make anyone feel left out.”

However, Sofia ended the relationship in August 2020, allegedly due to tension over Kourtney. The model went on to marry Elliot Grainge in 2023, while Scott has yet to walk down the aisle.

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Are Kendall Jenner And Scott Disick Close These Days?

While Kendall and Scott have seemed to remain friends despite his break-up from Kourtney in 2015, the duo still have their ups and downs, as evidenced during an episode of The Kardashians that aired in 2022. The episode showed Kendall accusing Scott of “villainizing everybody,” as he’s struggled seeing Kourtney move on in her marriage to Blink 182 drummer Travis Barker.

After Scott expressed feeling left out of the family after Travis entered the equation, Kendall tried to come to her sister’s defense. The argument escalated, leading the model to leave the family dinner while Scott continued to complain about how the family treats him differently nowadays.
“Kendall’s stuck in the middle so that’s not fair to do to her, either. She feels terrible … you can’t make somebody do or feel what you want them to do. It’s only gonna get better and better,” Matriarch Kris Jenner said of the situation.
Fans will notice that Scott has been less present on The Kardashians, as his relationship to the Kardashian-Jenner family has changed since his split from Kourtney. Nevertheless, as he’s the dad to Kourtney’s three oldest children, Scott will always have a place in the family, and he’ll always been in their lives, including Kendall’s.