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If it's an Aveirah to hurt a fellow Jew's feelings, is it likewise an Aveirah to hurt your own feelings? (e.g. via self-deprecation?)

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    מועדים לשמחה. Regarding discussion of a potential prohibition against embarrassing oneself, see Bava Kama 91. As far as a general duty to be kind to oneself, M'tzudas David (Mishlei 11:17) indicates that showing kindness to oneself is a prerequisite to showing kindness to others, and Rashi based on the same verse implies that showing kindness to oneself is included in the obligation of lovingkindness (Shabbos 127b, s.v. ה"ג הני נמי בהני שייכי).
    – Fred
    Apr 9, 2023 at 8:43

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Great question!

I think we can answer this question with another question :)

Can one say lashon hara about oneself? See here and here for opinions on this matter. So whoever’s opinion you follow regarding this issue I believe it would determine if Onaat Devarim applies to oneself, and likewise would determine if it's an aveirah. Just to add that one of the points mentioned by Rav Aryeh Lebowitz was that the Chafetz Chaim implies in two places in his sefer Chaftez Chaim (1:9, 7:6) that there is no lashon hara on oneself. (I bring this up because there is no stronger proof then bringing the answer from the Chafetz Chaim himself, and likewise it wouldn't be an aveirah).

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