Basically, do you have a Venmo account I can use?
As a general rule, it’s not a good idea to keep tabs on loved ones because nobody likes a cheapskate. If you cover the bill for them occasionally — especially if you can afford to do so — you shouldn’t make a big deal out of it or ask for repayment unless you’ve lent them a substantial sum of money.
Someone obviously didn’t get the memo. He repaid his wife’s mom for a $4 soda. It would be impolite and tasteless regardless of whether or not he was as wealthy as the OP claims. The fact that his income is over $500,000 per year makes the situation even more intolerable.
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