As Rosh Hashanah approaches, something is weighing on my conscience. I happen to know that a friend of mine, who is now a wonderful person, has a very checkered past that he is not proud of. I once mentioned this to a mutual friend. I know I shouldn't have gossiped, but I did. Now I have a quandary: if I ask forgiveness from the person about whom I spoke, I will feel much better, but it will embarrass him immensely to find out that people have been gossiping about him. So what am I supposed to do?


When we have wronged another human being, even if he or she does not know about it, the only way we can make amends is by apologizing to that person. G‑d will forgive us for sins we do against Him, but He will not forgive a wrong committed against a fellow human being until we have asked the hurt party to forgive us.

This request should preferably be made in person—so don’t just text or WhatsApp your friend. The sages of the Talmud felt that messages were too flippant to qualify as a sincere apology. True forgiveness happens in the discomfort of a face-to-face encounter. The awkwardness of facing up to the one you hurt is in itself a cleansing of your soul for the wrong you did. (Of course, if circumstances prevent you from seeking forgiveness in person, you can make a phone call or write a letter.)

And yet, if the act of asking forgiveness will itself be a cause of pain to the person being asked, it is wrong to do so. You have no right to allay your own guilt at the expense of another person's dignity. Asking forgiveness is not about bringing a sense of closure for yourself, it is about doing the right thing. You said hurtful words, and that cannot be fixed by saying more hurtful words.

There is a possible solution. Ask the hurt party for general forgiveness, without specifying the embarrassing details ("Please forgive me for any wrong I may have done to you").

This is not ideal. The other person doesn’t know what he or she is forgiving you for, and you are getting away with not owning up to the misdeed. But you will have to live with that, rather than unburdening yourself by humiliating someone else.

We can't take back our words. But we can prevent ourselves from talking negatively by engaging in positive speech. So speak favorably about people, catch them doing the right thing, expose their better side. Talk is not cheap. Use it wisely.

Shulchan Aruch Harav, Orech Chaim 606:1