Sorry

I’m told that it’s best to tell someone you’re sorry when you mess up. But what if you already know the person would rather not hear it, do you still apologize?

Does Apologizing to someone who resents hearing the apology negate the purpose of apologizing?

I was once told, “Esther, I wish you would quit apologizing to me. You know you are doing this for yourself right? This isn’t helping me at all.” (This was said very shut-up-and-go-away Esther-you-are-bothering-me way.)

I have since tried extra hard to avoid conflict with said person in an effort not to mess up. Because I think they were at least partially right. It is sort of engrained in me; I can’t forgive myself properly without working things through.

So:
It’s been several years.
I have (perhaps royally) misspoken and offended/hurt this person again.

Wasn't intentional and I’m not sure—but the offense taken was maybe exaggerated by the 3rd party. Still is very troubling, and I Know That I Could've Worded Things Better.

Usually it’s best for me to talk things out, but in this case if I am just annoying them... Rather than talk things out I might be better off to shut up and pretend no one told me they had taken offence at my words.

So

Sad.