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Praising a Bad Purchase

It is true that if a friend buy something new, I should congratulate him and tell that it was a good decision just to make him feel good? Even if a disagree with that? Or I should tell him the truth about what I'm thinking?

Answer:

You should congratulate him, and tell him how good the purchase is, even when it really isn't that great -- but make sure you sound sincere.

The source for this is a Gemara in Kesubos (17a), which cites the words of Beis Hillel assuming that when a person makes a bad purchase from the market, one should certainly praise it, rather than telling the truth.

This is also the halachic ruling with regard to praising a bride on her wedding day.

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