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Timid vs timing?

When is it ok to be fed up with something or someone and just say "fuck it!" What extent is reasonable for one to venture to without breaking common moral? You get cheated on multiple times by multiple partners is it feasible to become promiscuous yourself? You have items and heirlooms stolen and taken from you time and time again. Does that justify stenginess and selfishness? Everyone has a breaking point of things they can handle. What is reasonable retaliation for reaching said emotional and mental status?
Timid vs timing?
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