Drake has been friends with the Jenner family for a long time.
Now he may be tapping its richest member.
A source tells PEOPLE that Drizzy has been seeing makeup mogul Kylie Jenner "romantically." Jenner recently broke up with Travis Scott, the father of her child.
Other sources deny the relationship is "romantic" but concede the two have been spending a lot of time together lately.
Kylie was spotted flirting with Drake at his 33 birthday party and they were together again at Drake's Halloween party, staying "super late."
If things progress between Drake and Kylie, he may one day be Kanye West and Kim Kardashian's brother-in-law, which will be interesting considering his relationship with both of those famous people.
Are you buying Drake x Kylie?