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Question: I'm one of four good friends who rent a house together. Last fall one of us lost her job. Amy pays rent from her savings, but whenever we all go out, the other three of us always pick up her tab. Amy's not close to finding a new job, and this is getting expensive. When can we stop?

Answer: You and your roommates have been exceedingly generous with Amy. But times are tough, and now it's time for some tough love. Being unemployed doesn't make someone a charity. When cash isn't flowing, she needs to cut back on certain things. At the top of the list: new clothes, nights on the town and all but the most frugal travel. Once Amy finds a job, she can go back to hitting her favorite clubs and restaurants as her new budget permits.

Of course, telling her you're putting the brakes on the gravy train won't be easy. In our experience, those folks who are most comfortable accepting the kindnesses of others are often the most wounded - unjustifiably wounded, but wounded nevertheless - when the free-lunch window closes. You might try softening the blow by making plans to do things together that Amy can afford right now. Netflix, anyone?

Questions? Email Money Magazine’s ethicists – authors of “Isn’t It Their Turn to Pick Up the Check?” (Free Press) – at