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If we are talking family; Mom/Dad (in-law), Grandma/Dad never pays the bill. It's split evenly among all the kids birthday or not. Also dose not matter if your sister/brother has more kids it's split evenly.
But the oldest pays the whole bill and cash or venmo - or the oldest just covers everything.
You also need new friends - Most of mines is spot on if the bill is like 1-300$ they will cover this bill and ill get the next. Anything more then we will split 50/50 or venmo the other 1/2. If cash is on hand i'll cover the tip. (not including outsiders)
In my work environment I always pick up the tab; unless we are with the owner.
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