As Scott Disick‘s bond with Khloé Kardashian has grown over the years — so have his public displays of flirtation.
The pair got off to a rough start when Disick started dating Kourtney Kardashian in 2006. Keeping Up With the Kardashians viewers saw Khloé voice her worries that her sister’s then-boyfriend wasn’t the right match. Disick and Kourtney went on to have three kids: Mason (born in 2009), Penelope (born in 2012) and Reign (born in 2014).
Even though the Poosh founder’s romance with Disick came to an end in 2015 after nearly one decade together, his friendship with Khloe only got stronger and more flirty on social media.
“Khloé and Scott have a very good relationship,” a source exclusively told Us Weekly in December 2021. “He speaks highly of her. They have a true connection. You can see when they’re together and it really shows.”
According to the source, Disick knows that Khloé “will always be there for him” while he offers his support to her as well, adding, “He’s kind and genuinely cares about her.”
Scroll down for more of Disick’s flirty exchanges with Khloé:
March 2019
“Been waiting all week to post this #wcw,” Disick captioned a shot of Khloé in a see-through fishnet bodysuit. The Strong Looks Better Naked author “liked” the photo and wrote, “Hahaha!! I love you Scott!”
November 2020
After Khloé posted an Instagram photo of her sitting in a chair, Disick wrote, “Love that chair. Love [you] in it even more [though].”
March 2021
While promoting her new collection, the reality star took to social media to show herself wearing nothing but a pair of mom-style jeans.
Disick was quick to show his support in the comments section, writing, “Wow.” He also added a fire emoji.
June 2021
In response to a social media user asking “Who is she?!” on one of Khloé’s posts, Scott replied, “Who isn’t she? That’s the question!”
December 2021
The Flip It Like Disick gushed over an Instagram photo of Khloé, writing in the comments section, “Fine American.”
The Good American cofounder replied, “@letthelordbewithyou haha!”
February 2022
After Khloé posted an Instagram snap of her wearing Kim Kardashian’s Skims brand, Disick responded, “Looking 2 fine 🔥.”
April 2022
“God must have broke the mold when he made you,” Disick told Khloé during The Kardashians premiere episode. “Get these cameras out of here and go upstairs then.”
Khloé, for her part, reflected on her past with her older sister’s ex, saying, “We did not always have a great relationship. I have gone to anger management over Scott, but somehow Scott and I became, like, besties. He really is like a brother to me.”
She added: “That being said, he does speak to me, maybe, a little more flirty than my real brother does. The whole thing is f–king weird.”
May 2022
During an episode of The Kardashians, Disick had nothing but compliments for Khloé when she helped him clean up a mess on his kitchen floor.
“Do your thing. You look hot. I would hire you as, like, a hot maid. A topless maid or something,” he joked. After Khloé pointed out that she “wouldn’t be topless,” the New York native added, “You would be bottomless.”
Disick also poked fun at assumptions that he would date Khloé following Kourtney’s engagement to Barker.
“We’re still brother and sister,” the California native reminded him, to which Disick replied, “I was just kidding. I was going to go for Kim anyway.”
May 2022
In response to Khloé showing off her new Talentless hoodies and legging, Disick wrote via his Instagram Story, “Wear it well with that body Khlo.”
June 2022
During an episode of The Kardashians, Khloé offered Disick a chocolate covered gummy bear, to which he responded, “Only if it is going in your mouth and you know what I am talking about.”
May 2023
During season 3 of The Kardashians, Disick joked about taking Khloé on a date. “Why don’t we go on a date so you can see what it is like? So you get the practice and then when you meet somebody …,” he said.
June 2025
Disick shared a flirty message after seeing her attire for Jeff Bezos’ wedding in Italy.
“God must have broke the mold when he made you!” Disick wrote via Instagram comment. “Get it my khlobird 🔥🔥🔥🔥.”
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