All the Times Scott Disick Has Flirted With Kourtney Kardashian on Social Media Since Their Split

Credit: Scott Roth/Invision/AP/Shutterstock

All the Times Scott Disick Has Flirted With Kourtney Kardashian on Social Media Since Their Split

Shooting his shot? Despite their rocky history together, Scott Disick and Kourtney Kardashian aren't afraid to get a little flirty on social media. 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. [jwplayer IYs8HGBe-l3ahXupL] "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. [podcast_block]

Credit: Scott Roth/Invision/AP/Shutterstock

All the Times Scott Disick Has Flirted With Kourtney Kardashian on Social Media Since Their Split

Shooting his shot? Despite their rocky history together, Scott Disick and Kourtney Kardashian aren't afraid to get a little flirty on social media. 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. [jwplayer IYs8HGBe-l3ahXupL] "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. [podcast_block]

Credit: INFphoto.com/INSTAR

April 2016

Nearly one year after splitting in July 2015, the Talentless clothing designer shared a throwback PDA photo in honor of Kardashian's birthday. "Everyone who knows you loves you so much!" Disick wrote alongside the snapshot of himself locking lips with his ex in the ocean.

Credit: Courtesy of Scott Disick/Instagram

January 2017

While the exes continued to work on their coparenting relationship, they traveled the world as a family of five. Disick shared a behind-the-scenes moment from one of their many vacations together, teasing that the Poosh founder was a "fly or die type," hinting that they were each other's ride or die partners.

Credit: Courtesy of Kourtney Kardashian/Instagram

April 2017

After sharing a handful of pictures from her travels with Disick in April 2017, the reality star clarified the state of her relationship with her ex with a flirty selfie. "MOM and DAD back at it again with the coparenting skills," she wrote via Instagram. Disick "liked" the photo soon after.

Credit: Broadimage/Shutterstock

December 2018

The New York native sent fans into a frenzy after posting a photo on social media that seemingly showed his then-girlfriend, Sofia Richie, relaxing in a pool with Kardashian standing in the yard behind her. "This looks nice," he wrote alongside the since-deleted Instagram post. Days earlier, Kardashian shared a racy photo of herself "coparenting" on a bed with Disick sitting nearby. 

Credit: Backgrid/MEGA

December 2018

"What more can a guy ask for," Disick captioned a photo of himself lounging poolside between Kardashian and Richie, confirming fans' previous speculation that he was spending time with both women. "THREE'S COMPANY."

Credit: Broadimage/Shutterstock

April 2020

While rumors of relationship trouble with Richie continued to swirl around Disick, he was caught "liking" an old photo of him packing on the PDA with Kardashian shared by a fan account in April 2020.

Credit: Courtesy of Kourtney Kardashian/Instagram

June 2020

Eagle-eyed Kardashian fans noticed that a piece of clothing worn by the mother of three in a June 2020 picture looked very familiar. While enjoying a lengthy stay at a Wyoming ranch, the reality TV personality cozied up to a baby goat in a blue and red flannel shirt that her followers suspected belonged to Disick.

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June 2020

Weeks after sparking rumors that the former flames were sharing clothes, Disick decided to poke fun at the fans hoping for a reconciliation between him and his ex. "Cute shirt," he playfully commented on another one of Kardashian's Wyoming snapshots.

Credit: Seth Browarnik/startraksphoto.com

July 2020

Making a move? The entrepreneur fueled reunion rumors even further when he was caught "liking" his ex's steamy bikini pictures more than one month after his split from Richie.

Credit: Courtesy Kourtney Kardashian/Instagram

August 2020

After a trip to the lake with friends, Kardashian shared a sexy snap of her silver one-piece swimsuit. “Lake ya,” she captioned the pic. Disick replied in the Instagram comments section, writing, “What a lake er.”

Credit: Kcr/Shutterstock;Matt Baron/Shutterstock

April 2021

After the Poosh founder's new boyfriend, Travis Barker, shared a PDA-filled series of photos to celebrate her 42nd birthday, Disick took to his Instagram Stories to post his own well wishes. "Happy birthday to the best mom a child could ask for and some more!" he wrote, along with a photo of the pair with their three children.