On Sunday, August 21, the reality star was photographed holding hands the blonde beauty as they left Santa Monica hotspot Giorgio Baldi.
Though the pair didn't kiss in front of the cameras, they certainly weren't trying to hide, as the dad-of-three, 37, stood out in a bright blue baseball cap, plaid shirt and black pants, while his date, 43, looked on trend in a low-cut black top, black leggings and heeled black leather boots.
The stars also have some history, as they were initially linked back in 2015 after Disick and Kourtney Kardashian ended their on-off romance. They've also run in the same circles, as her dad is famed singer Rod Stewart, and Kimberly works as a closet organizer for high-end clients and celebs.
In fact, she took to Instagram this spring to reveal she organized Disick's abode, and her father even came out to see the results.
Disick has been playing the field since his and Rebecca Donaldson's romance fizzled in June after just a few months. As OK! reported, the model was the one to call it off since she didn't see a future with the Talentless founder.
"Rebecca told Scott that he will never be able to be serious with anyone until he gets over Kourtney and that she needed to move on. Getting caught up in his world was not what she wanted," explained the source. "Scott understood where she was coming from and he respects her for being honest with him."
Multiple sources have claimed the Flip It Like Disick lead still harbors feelings for 43-year-old Kardashian, the mother of his children, and since she just tied the knot with musician Travis Barker, 46, he hasn't been taking things "well."
"He's spending time with friends ... to keep his mind off of it," said and insider. "It's been hard for him to process and digest even though he knew it was coming."