You are walking down the street when you pass an old friend whose head is down, a deep frown etched on her face. You instinctively say to her, “Cheer up,” hoping to lift her spirits.

Well, it won’t. It will, however, make her angry, frustrated and more depressed. You are being an insensitive boor and you don’t even know it. If that’s all you’ve got to say, keep quiet and offer a friendly smile, not a trite comment. If I am going through a hard time, I don’t want someone to tell me to be cheerful—I want someone to understand why I am miserable.

“Cheer up” implies that I have no reason for feeling bad. Let’s face it: chances are that I’m not sad for the sheer fun of it. Something is obviously troubling me, causing me to be melancholy. Telling me to cheer up is effectively denying me the right to feel upset about it. Imagine the burden I now carry: I not only have a worrying problem, I’m not even allowed to feel bad about it!

It is also an insult to imply that becoming cheerful is simple and easy. It is like saying, “What’s wrong with you? Pull yourself together.” When someone is depressed—over finances, a troubled marriage, or whatever—the last thing they want is to be made to feel inadequate for feeling low. If it were that easy for them, they would have cheered up without your sage advice.

Take a leaf out of the book of the biblical Joseph. He was languishing in an Egyptian jail with two of Pharaoh’s ministers, when one morning he notices they are in a foul mood. What does Joseph tell them? Does he tell them, “Chin up”? Actually, he doesn’t tell them anything—instead he asks them a question: “Why are you sad today?” which is their cue to unburden themselves to Joseph.

Joseph did something very profound. He didn’t tell them how to feel; instead he gave them an opportunity to talk about their problems. Joseph realized that in 99% of cases people are upset for a reason. The way to help them is to encourage them to talk about the problem and to help them work towards a solution.

So on the next occasion that you are tempted to tell another to “cheer up,” consider that perhaps you are merely furthering his or her misery with your insensitive remark. Here is a simple rule: when something is the matter with another person, it is almost always better for them to do the talking, not you. Whatever your huge brain conjures up will almost certainly be irrelevant, and potentially offensive.

When you ask someone, “How are you?” are you really prepared to wait for the answer? That is the real reason we say “cheer up”—it is quick and easy. We convince ourselves that with our nugget of wisdom we have done our part for humanity, while in reality the recipient of your brilliant aphorism is bursting inside, “I hate you for saying that!”

Remember, once the words have gone out, they cannot be put back in. Maimonides wisely advised not to say anything without reviewing it in one’s own mind three or four times. On these occasions five or six would not be amiss, and assiduously observe the rule: if in doubt, say naught.

If you care about someone going through a rough patch, find some time to listen. If you are not good at listening, offer a hug or—very Jewishly—a cake . . .