This is probably more an issue with your craven, confrontation-fearing friends than the technology that lets you smoothly settle debts without relying on the old memory-based balance sheet, which has a way of selectively omitting items.
Let the next miserly Venmo request serve as the impetus to start communicating clearly and tactfully about spending money with your friends, which isn t easy, but is probably a large part of being a socially functional adult.
Tastefully avoid talking about money is not a social grace worth keeping around for many reasons, but especially because it tends to punish those with less money.
One overdone-but-still-true example: Wordlessly splitting the check might have a grad student who strategically ordered soup subsidizing his private equity pal s jewel-encrusted truffle-oysters.
Initially it might feel icky to make every social outing explicitly about the transactions, but that same ickiness drives people to never addressing these issues directly, which feeds more resentment on one side and more obliviousness on the other.
If the choice is between normalizing money-talk versus repressing it for fear that it will taint the purity of your sacred hangout session, then I m working towards the former.