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. The Revenge Body host previously used her platform to show her appreciation for the businessman.
“Happy birthday to my brother @letthelordbewithyou !!! I am so thankful to have such an incredible addition such as you to our family! We have come such a long way, you and I! I am so thankful for the person that you have grown into,” she wrote via Instagram in May 2019. “I am thankful for every highs and lows because we have been through it all and we are closer than ever. I am proud to say that you are my brother and also one of my best friends! Have the best birthday Lord!! FOREVER the Lord and the Lady.”
At the time, a follower questioned the twosome’s connection, writing, “Refuse to believe they’ve never shagged.”
Khloé, for her part, clapped back, “The comment you made makes me feel sad for you. I feel sad for you because apparently you don’t have relationships in your life that can be completely platonic. You don’t have relationships where someone genuinely loves and cares about you without wanting anything else besides a friendship.”
“Khloé and Scott have a very good relationship,” the insider revealed in December 2021, less than two months after Kourtney announced her engagement. “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: