Song meaning of Chicago Freestyle by Drake (Ft. GIVĒON)

Well, well, well, looks like Drake is back at it again with his confusing lyrics in "Chicago Freestyle". So, we have Drake flying around in a truck, switching to a plane, then a hotel lobby, and eventually ending up in the Windy City. He's clearly on the prowl for girls with his Galleria credit card swipes and all-access backstage passes. But he can't seem to make up his mind on the ladies, treating one girl too nice and swiping left on another one who has a man. Meanwhile, Drake's just trying to have a nice night and show his girl some images that last. I guess that's supposed to be romantic? But then he admits he's done plenty of sinning in the past, which doesn't exactly scream boyfriend material. And despite all this, he's still wondering if he'll see his girl at the show and holding out hope that maybe they'll grow to love each other. I'm sorry, Drake, but one thing I do know for sure is that you need to get it together, my man.