On Monday night, prior to their flight, the superstars stepped out for a dinner date at Nobu in New York City.
An eyewitness tells ET that Rihanna stayed at Drake’s hotel overnight on Sunday after winning the Michael Jackson Video Vanguard Award at the MTV Video Music Awards.
Aside from simply enjoying dating a more experienced woman, Drake said he was drawn to her perspective — she framed the world much differently than he did at the time. I think I can also maybe even say I felt guilty to the fact that it was a bit of a story to tell, that's why I was doing it. I never end up dating — seriously — women that are my age." The Lil Wayne protégé went on to add that more often than not he finds himself in relationships with women pushing 30.
Well, it turns out there is, if you're willing to do an insane amount of work.
I had the DJBooth squad listen to every Drake song we could find - we're talking every project from , plus guest verses, and we wrote down every time he mentioned a woman in the romantic/sexual sense.
Drake extended his holiday weekend with Hailey Baldwin by getting cozy with her on a date ...
the night after they hung out at his insane house party.