When is "I'm sorry" not enough?

When the person saying it: hasn't really changed, doesn't really understand what the problem is but doesn't want you to be mad anymore, doesn't have the patience or the strength of character to take the small steps to rebuild the trust in your relationship, cannot love you enough to let you go if the wounds are too deep, is saying they are sorry to avoid consequences or to further manipulate you.

For a really good book on the subject, I highly recommend "Boundaries Face to Face" by Henry Cloud and John Townsend.

If you are working through a relationship with someone who is using apologies to manipulate you, please get into counseling with someone. You need a real live person to listen to you and support you when you set limits with that person.

Very good question. Simply put, "sorry" is not enough, when someone you are very close to does something so unforgivable that it doesn't matter what they say or do, there will always be that one thing you always think about.

For example, if your best friend in the whole world betrays you in some way and does something that you would never consider EVER doing to them barring a gun put to your head. How can you ever trust them again? They can apologize and apologize and you can forgive them and understand what they did, but nothing will EVER be enough. Even if they save your life the next day. This is because how can you trust them again? How can you know that they feel the same way about you the way you about them? There may be a friend you would do anything for. How can you deal with the fact they may not do the same for you, and would betray you without a second thought. This gives rise to sayings like a friend "stabbed me in the back." This scenario also goes for cheating couples. A "sorry" will never be enough. I'm not saying you can't still be friends or you still can't get married or forgive and forget (whichever situation), but there will be always be that SOMETHING that you think about and you may never be able to fully trust them again.

Your sorry is not enough when you cross the line.

For e.g. -you know about the law and you still do things like still, cheating on your husband/wife, molesting, rape or killing.

Or if you've been told, ask not to do something, maybe the first time if not serious, can be ignored depending on the affect of what you've done.

But if you do it again, I do not think sorry is enough at this point, because you've done it before.

There are some things where sorry is not enough even for the first time. Some you can say sorry more than once.

Cheers

Well, my personal opinion is , I'm sorry is never enough.It doesn't matter if someone accidently dropped a sticky piece of candy on you new carpet, or if you boyfriend cheated on you with someone you know and love.The truth is, it doesn't really matter what the situation is.You can't just say I'm Sorry.You have to be sincere about it and show that you really mean it.Good Luck with whatever your problem is.I hope things turn out for the best.

In some dating scenarios. For example, girl, if you betrayed a bf once and he asked you to never do it again, and you said you wouldn't, then some months later, you break that promise, even though he trusted you, "I'm sorry " isn't enough, nor is it likely to be believed. For another example of when it's not enough, read/re-read Peter And The Wolf.

When the problem keeps recurring, when abuse happens, whent he person is cheating, when your lover is making not much of a secret of his flirting, talking to other women like he talks to you,

so many things...

Since we are commanded to forgive -- "And when you stand praying, forgive whatever you have against anyone; in order that your Father who is in the heavens may also forgive you your trespasses." (Mark 11:25) -- The only time sorry isn't enough is when they don't mean it. :)

EXPOUND. HAHAHA.

When you've killed someone or destroyed something they loved, cheated on them, etc.

Of course it depends on the situation/person combination.

'When something is unforgiveable' is just repeating the question.

I'm sorry is not enough if the person is not willing to change or stop what they have done that is wrong. If they continue to do it then, they are not sorry.

When it has to be said over and over and over again. Sooner or later you have to start meaning it and make some changes.