"Here's the thing: You don't actually know what's in your friend's bank account. She may have come into an inheritance, have a generous child helping her out, or simply have her finances more under control than you assume. Making decisions based on guesses about someone else's financial situation is a risky game, and it can quietly become its own kind of condescension."
"So stop the dinner bill tussle and propose a new system. The simplest: just split the check every time. Before the bill even arrives, make it the default understanding between you. No negotiation, no awkwardness, no one feeling pitied or managed. If that feels too rigid, the next best option is trading off—you get this one, she gets the next."
A retired teacher repeatedly offers to pay for shared lunches, creating an awkward tussle when the bill arrives. The payer's actual financial situation is unknown; she may have savings, an inheritance, or family support. Making assumptions about another person's money is risky and can feel condescending. Establishing a clear system avoids discomfort: split the check every time, or alternate who pays. Set the default before the bill appears so no negotiation or awkwardness occurs. Allow spontaneous treats for birthdays or special occasions, but otherwise maintain the chosen routine to preserve the friendship and mutual respect.
Read at Slate Magazine
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