What I worry about is that Venmo is an expression of "everybody is too poor to actually cover each other", and that's a damn shame if true.
The way we, now aged, uncool, unhip folks used to deal with this was that we would cover people like you discreetly.
One of the better off folks (read: professional receiving a paycheck rather than starving grad student) would take charge of the "pot", would figure out what was lacking and generally "tell" a couple of the other better off folks what to put in. I never had an issue covering an entire bill for someone and neither did any of the other folks. 1) We asked you to join us because we appreciate your company and 2) people probably did this for us when we were the poor ones.
This works very well unless you have someone freeriding who shouldn't (we had two people in our group who were really well-paid programmers who did this). When that happens, I would itemize the free-rider in excruciating detail and if he didn't put in every red cent, I would call him out on it.
I think this really speaks to the issue - by making things quick, easy, and fair-with-documentation, we lose out on the opportunity to practice a bunch of hard-to-relearn (and imo valuable) social skills and machinery that comes with interpersonal debts. see Graeber - https://en.wikipedia.org/wiki/Debt:_The_First_5000_Years
The way we, now aged, uncool, unhip folks used to deal with this was that we would cover people like you discreetly.
One of the better off folks (read: professional receiving a paycheck rather than starving grad student) would take charge of the "pot", would figure out what was lacking and generally "tell" a couple of the other better off folks what to put in. I never had an issue covering an entire bill for someone and neither did any of the other folks. 1) We asked you to join us because we appreciate your company and 2) people probably did this for us when we were the poor ones.
This works very well unless you have someone freeriding who shouldn't (we had two people in our group who were really well-paid programmers who did this). When that happens, I would itemize the free-rider in excruciating detail and if he didn't put in every red cent, I would call him out on it.