Not in my neck of the woods. If you sent a Venmo request amongst us you would be invariably called an asshole (and it wouldn't be a kind way of saying it, that sort of thing is real shitty). We use Venmo to push money around (Square Cash is nicer, but that ship has sailed), but it's more like "ehh, $25 is about right and I'll get it next time so the rounding will work in my favor".
We are not doing down-to-the-penny nonsense because that would be silly and we are not dunning our friends because that would be awful.