Introducing Pay Dirt, Slate’s new money advice column.
I have a friend who’s always been a little cheap with shared checks. If I throw my card down for ease and let people Venmo me, he’ll pay me, like, a conservative estimate of his portion and also not take tax or tip into account. I always kind of forget about this until he does it again. A few months ago, he estimated $25 when he owed me $40, and I was like, “Bro,” and he seemed perplexed and gave me the $40.
Another possibility is that your friend has family money coming but is not benefiting from it at the moment. I say this, having bought many a $3 happy hour beer for underemployed friends in my 20s who had trust funds but couldn’t access them yet and whose parents did not subsidize them in the hopes that they would learn to be independent. I was not obligated to do that, and neither are you, but it could explain why your friend appears to be pinching his pennies.
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