Another source claimed Kylie Cosmetics founder and the 33-year-old were "enjoying each other's company," adding:
"They were joking around and Kylie was laughing. She seemed to be really happy and in a great mood and her and Drake seemed very comfortable with each other. There seemed to be an attraction there."
Last week, Kylie also made an appearance at Drake's Halloween Party in West Hollywood, where she allegedly stayed "super late," according to The Cut.
Recently, Kylie called it quits with Travis Scott, with whom she shares daughter Stormi Webster.
Drake - who also has a child named Adonis - has something of a tumultuous past with the Kardashian family.
The One Dance singer was a regular guest at Kardashian-Jenner birthday parties and family dinners (he even performed at Kylie's 16th birthday party in 2016).
However, earlier this year, Drake was in conflict with Kylie's sister, Kim Kardashian West and her husband, Kanye West after he accused Kanye of leaking the news of his secret son.
The couple later accused Drake of threatening their family in a series of tweets following the debacle.
With Kylie now rumoured to be romancing Drake, things may become awkward at the next Kardashian family event.
