Scott Disick’s Flirty and NSFW . to Khloe Kardashian

Scott Disick and Khloé Kardashian became best buds during his nine-year on-again, off-again relationship with Kourtney Kardashian. Fans often enjoyed watching the two whip up trouble on the family’s hit shows on E! and Hulu, but Scott’s banter has turned flirty toward the Good American founder over the years.

“We did not always have a great relationship. I have gone to anger management over Scott. But, somehow, Scott and I became, like, besties and he really is like a brother to me,” Khloé said during the series premiere of The Kardashians. “That being said, he does speak to me, maybe, a little more flirty than my real brother [Rob Kardashian] does. The whole thing is f–king weird.”

Keep scrolling to see Scott’s flirty and NSFW comments to Khloé over the years.