I try not to be that guy, but I have a lot of friends like this (will literally venmo charge you in the moment). It just makes the relationship feel transactional.
I always try to be the one that initiates a good faith system so people can get a feel for what I'm about. Worst case is someone tries to take advantage of me, but by then their (lack of) character shows up in other ways
I’ve never had a friend like this, and I never will. I don’t mean to say I haven’t met people like this, but they have no chance of becoming my friends.
I think there’s a difference between asking for exact change and just rounding up to quickly pay someone back. It’s not immoral or anything to use venmo to square up obligations, but it does feel petty once you bust out a calculator or use exact change.