Cheef is the slang for smoking weed.
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You only live once, might as well go hard while you’re young.
Here he is referring to the time when he spent $300 on prostitutes in Amsterdam while still having a girlfriend back home which he felt somewhat regretful about it.
He then contradicts the the previous line and shows us how strongly his friends feel about him leaving.
He is pondering whether or not his friends would still be around if he left to do his own thing and came back one day.
In other words, he never wants to be drawn into the “friend-zone” again because he learnt from his first mistake.
On the other hand, he doesn’t want to be seen as a failure or a loser if he makes a mistake or fails at something.
When he works hard and succeeds, people around him notice that and praise him for it.
In other words, when he puts time and effort into his music, he can make great things happen.
She used to be a happy, innocent girl who loved spacing out and enjoying the simple things, but now she feels like a prisoner sitting in her own dull room.