How many times do I have to say I’m sorry before it gets through? Will it ever get through?
— Always Sorry
Always Sorry: Probably not, but that’s not the part of the problem you’re responsible for.
Stop apologizing for things you’ve already said you were sorry for doing.
Instead, when the past wrongs come up again, start asking questions:
“I apologized for that when it happened, as you may recall. Is this still an open issue? Do you believe my apology wasn’t sincere?”
Get at the root. That question will force your friend to say either that they believed it was sincere, thus putting the issue to rest, or they believed it wasn’t sincere, thus allowing you to say, “I’m sorry to hear that. I don’t know how you can stay friends with me believing I’d lie to you like that.”
This is their reckoning to have, not yours. Make that clear and step away to give them a chance to figure it out. What you’re doing now, the apologizing and re-apologizing every time they demand it, allows them to weaponize this vulnerability of yours against you in a fight. It also doesn’t speak well of them.
That reckoning is yours to have — with continuing a friendship that involves having all your old mistakes dredged up and used against you. When you’re ready to take this on, feel free to say, calmly: “If you are genuinely still upset about all these old arguments, then please let me know what you would need from me to allow you to put them to rest.” Don’t budge.
If their answer is vague or if they say they’re over the old mistakes, then say, just as steadily: “Okay then. Please do me the favor of not bringing these incidents back up the next time you’re upset, unless they’re directly relevant. Not because I feel guilty or want to escape responsibility, but because it’s not productive. I will show you the same courtesy in not revisiting times I’ve been angry at you.”
That way, if they do this to you again, you’ve laid the foundation to tell them, “I won’t keep doing this. I’ll be happy to talk later, when you’ve had a chance to cool off.”
An argument can recur only if you agree to keep showing up to have it.