But as Kylie's camp rushed to dispel the rumours and reports that the makeup mogul is spending more time with her ex - what's really going on in Kylie's love life?
Drake, 33, has known the Kardashian-Jenner Klan for years and even performed at Kylie's 16th birthday party.
Rumours of them being a couple first ignited when Kylie recently attended the pop icon's birthday bash in Hollywood and it was reported that the pair "had an attraction".
Although some sources attempted to shut down rumours and insisted to the publication that Kylie and Drake's relationship is just "friendly", another insider told People the pair have been hanging out "romantically".
One report suggested that they got involved months ago and decided to keep it under the radar because of Drake's previous feud with her brother-in-law Kanye West .
The Sun claimed Kylie "wanted to keep the news from her sister Kim Kardashian who is married to West.
However, there's no suggestion that there was any overlap with Kylie's ex-boyfriend Travis Scott, the father of her daughter Stormi, who she split from this year.
Reports of their suspected blossoming romance had also reportedly upset Travis.
Hollywood Life claimed Travis would "feel betrayed" if Kylie and Drake's relationship actually became something more romantic.
It was then claimed that Drake dumped her because he is more of a "free spirit" and didn't want to be tied down.
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