I live in a transplant city dominated by young professionals. Multiple roommates (paying for utilities, grocery shopping together, house-shopping), many nights out a week with friends, etc. all yield to a multitude of spotting cash/credit for everyone.
The only assholes are the ones who freeload often. venmo keeps everyone in check.
I live in Boston, which is about as young-and-transplanty as it gets.
I don't know, maybe I just hang out with folks who take friendship with a degree of seriousness, but nobody I know would need to dun somebody in either our group or our extended group to pay their share. You grab the bill, you eyeball it for your stuff, you add twenty percent for tip, you're done.
If you try to freeload, you just wouldn't be invited again. Because friends don't do that, just as they don't send each other invoices.
The only assholes are the ones who freeload often. venmo keeps everyone in check.
What is your neck of the woods, partner?