What is required to truly be "sorry" for something? I've always heard that if your truly sorry for an action, you will never repeat that action. A repeat offence, therefore, means that you were never truly sorry in the first place. So how can one express sorrow?/what is required for a true "sorry"?

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If by 'feeling sorry' for an action, it is meant that the action is regretted, then it seems to me that one may sincerely regret an action and nevertheless for some reason commit a similar action. (That an agent repeats an action that s/he sincerely regretted may reveal something deep about the agent's character--for example, that s/he is unreflective--but I don't think that the fact of such a repetition undermines the sincerity of the agent's regret. After all, s/he certainly did feel regret, assuming that s/he correctly reported her feelings, and so the fact of her feeling regret cannot be called into question unless one is willing to attribute a very deep lack of self-knowledge to the agent.)

I think that some of the philosophical significance of this question arises from its connection with the nature of apology, a topic that has received some attention from philosophers, albeit less than one might think the topic merits, given its deep and pervasive importance to human relations. At least two issues may be distinguished here: first, what is it genuinely to apologize (and, hence, I think, to be sorry for what one has done)?; second, if one is sincere in one's apology, does it therefore follow that one must never commit another similar offence, without therefore undermining the sincerity of the apology? I think that these questions may be treated in reverse order.

To my mind, regardless of what it is sincerely to apologize for something, even if one sincerely apologizes, it doesn't therefore follow that one may never have to issue a similar apology again. (An agent may, upon reflection, come to regret and sincerely apologize for something that s/he did even if at some later date, s/he--presumably unreflectively--commits a similar action.) The deep question, I think, relates to the conditions on sincerely or genuinely apologizing: need one, in order sincerely to apologize, feel a certain way? I'm torn on this question. On the one hand, I am inclined to take apologies to be constituted by engaging in a certain sort of interaction, and hence, to be independent of thoughts (which are, after all, not accessible to the person to whom one is apologizing). On the other hand, however, it is common enough to feel that an apology is not genuine, because the one who apologizes doesn't really mean it. While I myself have felt this way, I'm not sure that I'm really justified in doing so. I just don't know how to adjudicate this issue.

For more on the topic of apology, you might check out Aaron Lazare, On Apology, or Jeffrie Murphy and Jean Hampton, Forgiveness and Mercy.

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