Would the never ask me for five bucks again if I have it to them?
Yep, they will never ask you again if you give it to them, otherwise they constantly ask you for as long as you live.
Surely not all seating is forbidden right? Sofas, wooden stumps are ok? Just no chairs.
Where should this comment appear?
This pairing only
Whenever "Give five bucks to someone to stop them from constantly ..." appears
Whenever "Live in a world without chairs" appears