That’s so true about stingy people feeling like they’ve been clever when they manage to wangle a freebie out of someone else!
At my old job, the company would stump up a fairly generous bar tab for people’s leaving drinks. One time we were out for such an occasion and we had a new guy with us who’d recently joined our team. He asked me quite early on whether he could get dinner in the pub, so I explained to him (VERY clearly) that the tab only covered drinks and that if he wanted food, he would need to buy it separately. He seemed fine with this.
A little later, the money ran out and one of the managers very kindly put his card behind the bar for an extra couple of hundred quid on the tab. Shortly after, a waitress came over with the most enormous steak dinner which the intern proceeded to eat on his own while everyone around him was just drinking. A little odd, but ok, maybe he was hungry.
Finally the tab ran out and some of us said we would go get dinner somewhere. The intern turns to me, beaming, and says ‘I don’t need dinner because I was smart enough to order something while the tab was still open! You lot missed out!’ He was so pleased with himself.
My manager checked his receipt the next day and sure enough, he’d paid £20 for this guy’s steak dinner. I suggested he say something but he felt too awkward and, ironically, thought it would make him look stingy if he did (he was earning more than the new guy, but not THAT much more).
That’s the other thing, I think these people rely on knowing that you’re unlikely to say something in case you end up looking like the petty one!