Lyric discussion by edbanky 

I am with sansmilk and feinsteins on this one. I believe "going down to the well" is synonymous with "having an orgasm." I think he is singing about conversing with a sexually experienced girlfriend figure, and he is curious about the actual feeling, being a virgin himself.

"what matter does it make, if there'll be favorite songs playing in my head" I think might be referring to a traditional desire to have your "first time" be special. Like maybe have some romantic music setting the mood, etc.

Incidentally, I don't think Charles Thompson sings about drugs much at all. And certainly not from some post addiction perspective. He mentions smoking pot, which he says he does occasionally, but, unlike those of so many "artists" whose lives are basically defined by self-imposed debauchery and addiction, I believe Charles' topics are rarely as uninteresting as "man, being addicted to ____ sucks."

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