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    That doesn't work. If the round is being paid for by someone else why would he care the size of it? And why would it "sound generous" if the person footing the bill isn't the person offering it? Commented May 2, 2020 at 9:25
  • The point is that "the drinks are on me" sounds generous, and under normal circumstances would be, but in an empty bar means nothing. Commented May 2, 2020 at 9:28
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    But he isn't saying "the drinks are on me" - he is saying "the drinks are on them". Under your analysis he might as well say "the drinks are on me" to get the credit for the empty gesture but that isn't the joke being asked about Commented May 2, 2020 at 9:30
  • It's by no means the best joke I've heard, and I think that it would work better if he were saying the drinks were on him, but the "empty gesture" aspect (whoever would have paid if there were people to buy drinks for) works sufficiently (for me) to be mildly amusing. Commented May 2, 2020 at 9:43