does this make sense or do I need to explain more?

Whichever it is I always end up with too many of those damn little wooden dowel things. Goddamn IKEA.
Were they during the medieval time period? Could he, perhaps, think this might be the case in a literal sense as a way to try to explain this to himself?
I don't see why not. Perhaps in this metaphor you participate in Mass in the Square, then enter the basilica to make confession and receive penance.
 
Is it clear what these euphemisms mean and why it's telling that he's surprised by the order in which they happen?
My concern is less about the euphemisms, more about the 21st feel of the language.

"Not in that order, come to think about it," and "sank into her chair," seem too modern day colloquial to my ear. Middle Ages, hard wooden benches, I'd have thought!
 
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