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You cannot really know if the other person minds; he might be saying he doesn't mind out of a desire to avoid conflict, for example. So let us first consider the case where we do actually know (as well as we can): can you say lashon hara about yourself? This question has been asked.

There is a famous story about the Chofetz Chayim saying this is forbidden. According to this answerthis answer, the Rav explains the prohibition thus (loose translation):

there's no novelty in saying that the Chofetz Chaim said that one cannot speak lashon hara about oneself (i.e. it's obviously prohibited), because after all, the whole concept of 'maris ayin' shows that a person doesn't have full jurisdiction over his own reputation to forgo it

You can't give up your reputation because it is not wholly yours to cede.

This answer also cites the Lubavicher Rebbe (6:1621) as forbidding it, saying that if it's forbidden to say it of others it's also forbidden to say it of yourself.

It seems to me that if you cannot say lashon hara about yourself, where you know the subject's intentions as well as any can be known, then surely you cannot say it about someone else, even if he says he doesn't mind.

You cannot really know if the other person minds; he might be saying he doesn't mind out of a desire to avoid conflict, for example. So let us first consider the case where we do actually know (as well as we can): can you say lashon hara about yourself? This question has been asked.

There is a famous story about the Chofetz Chayim saying this is forbidden. According to this answer, the Rav explains the prohibition thus (loose translation):

there's no novelty in saying that the Chofetz Chaim said that one cannot speak lashon hara about oneself (i.e. it's obviously prohibited), because after all, the whole concept of 'maris ayin' shows that a person doesn't have full jurisdiction over his own reputation to forgo it

You can't give up your reputation because it is not wholly yours to cede.

This answer also cites the Lubavicher Rebbe (6:1621) as forbidding it, saying that if it's forbidden to say it of others it's also forbidden to say it of yourself.

It seems to me that if you cannot say lashon hara about yourself, where you know the subject's intentions as well as any can be known, then surely you cannot say it about someone else, even if he says he doesn't mind.

You cannot really know if the other person minds; he might be saying he doesn't mind out of a desire to avoid conflict, for example. So let us first consider the case where we do actually know (as well as we can): can you say lashon hara about yourself? This question has been asked.

There is a famous story about the Chofetz Chayim saying this is forbidden. According to this answer, the Rav explains the prohibition thus (loose translation):

there's no novelty in saying that the Chofetz Chaim said that one cannot speak lashon hara about oneself (i.e. it's obviously prohibited), because after all, the whole concept of 'maris ayin' shows that a person doesn't have full jurisdiction over his own reputation to forgo it

You can't give up your reputation because it is not wholly yours to cede.

This answer also cites the Lubavicher Rebbe (6:1621) as forbidding it, saying that if it's forbidden to say it of others it's also forbidden to say it of yourself.

It seems to me that if you cannot say lashon hara about yourself, where you know the subject's intentions as well as any can be known, then surely you cannot say it about someone else, even if he says he doesn't mind.

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You cannot really know if the other person minds; he might be saying he doesn't mind out of a desire to avoid conflict, for example. So let us first consider the case where we do actually know (as well as we can): can you say lashon hara about yourself? This question has been asked.

There is a famous story about the Chofetz Chayim saying this is forbidden. According to this answer, the Rav explains the prohibition thus (loose translation):

there's no novelty in saying that the Chofetz Chaim said that one cannot speak lashon hara about oneself (i.e. it's obviously prohibited), because after all, the whole concept of 'maris ayin' shows that a person doesn't have full jurisdiction over his own reputation to forgo it

You can't give up your reputation because it is not wholly yours to cede.

This answer also cites the Lubavicher Rebbe (6:1621) as forbidding it, saying that if it's forbidden to say it of others it's also forbidden to say it of yourself.

It seems to me that if you cannot say lashon hara about yourself, where you know the subject's intentions as well as any can be known, then surely you cannot say it about someone else, even if he says he doesn't mind.