Assatry can only be used in two situations, yet the way it's used in a sentence may be identical in both:
When a situation is so incredibly bullshit that it has transcended into an entirely different form of ass.
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When one or more persons is continuing to do something so stupid its actually impressive.
Pajama casual is a term used when working from home and preparing for a video conference. All business above the waist and your pajama pants down below.