The Kesef Mishneh on Hilchos Teshuva 2:5 says that revealing a previously committed sin to someone who doesn’t know you’ve sinned is a chillul hashem. If that person knows you’ve done the sin before and you tell him a specific occurrence, is that also chillul hashem?

Example: someone who is known to have watched “rated R” films saying that they saw a specific film, or someone who is known to have eaten treif discussing a specific restaurant etc.

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    Follow your heart - will it make the people / the world better? – Al Berko Nov 5 '19 at 14:45
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    If it's not in a good purpose, it's perhaps as you speak about this without shame, a kind of effrontery – kouty Nov 5 '19 at 15:02
  • Something else to consider that People tend to forget - Lashon Hara applies to oneself as well & sharing experiences of previous sins definitely sounds like it's Lashon Hara – Lages Nov 5 '19 at 15:57

The reason it's a Chilul Hashem is that it's Chutzpa to brag (or even mention) that one went against Hashem's will.

It seems to me that going into specific details about a sin is similar to bragging; one should be so embarrassed about the sin that one doesn't want to discuss it in any detail.

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