Judging Mortal Sin

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It’s clear in the context of that sermon that he urging his audience to try and take the means of perseverance afterward, and not simply be absolved but change nothing. I think anyone who has had some repeated sin in their lives recognizes the difference and surely a priest does. And notice, he says “immediately”–clearly someone who, say, stole something from the local convenience store, went to confession, and then literally went directly to the store again to steal something again does not have the purpose of amendment. That’s what he is talking about and I am sure priests can recognize the difference.

Christ commands us to forgive our brother seven times seventy times (meaning an unlimited amount) because that is what God does for us.
 
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Thank you for your comments @anon90190422. They’re helping me think through this issue.

Because of some personal circumstances in my life I have thought a lot, in my own way, about this particular doctrine of the Church–and it really does seem to be a doctrine–that God gives sufficient grace to avoid mortal sin. My thoughts about this are the following:
  • I don’t believe anyone here has yet (as far as I can tell) rejected this doctrine. I certainly do not. I believe everyone receives grace sufficient to avoid mortal sin, and I think the others would agree with me.
  • The issue at hand is whether it is possible for someone to appear by all accounts to remain unrepentant in mortal sin to not be in mortal sin at all. And I think the answer is yes.
  • The doctrine of the Church is that God gives sufficient grace to avoid mortal sin, but I don’t think we as Catholics are required to believe that God gives sufficient grace to avoid grave matter.
  • That is to say, someone could be faithful to the promptings of grace their entire life and continue to commit gravely evil acts, on account of something in them which deprives them of the agency necessary for the commission of a mortal sin.
Of course I submit to people who know much more about this than I do. If I say anything wrong, please correct me. I would be happy to try to clarify anything I’ve written.
 
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With respect Father, Saint Alphonsus Liguori taught that if someone repeatedly falls into the same sin shortly after confession, they have lost the purpose of amendment, as they have not taken the necessary steps to avoid the occasions of sin. Thinking one could fall into sin is one thing, but the purpose of amendment must be firm and resolute, that one will never again commit mortal sin
That’s not quite how St Alphonsus put it. He does, quite rightly, ask whether the contrition of one who falls immediately into the same sins, after receiving absolution and certainly we should never presume God’s mercy or approach the sacrament of reconciliation casually. At the same time, that’s not to say that a person who repeatedly falls into the same sin lacks a firm purpose of amendment. For many people, the struggle with sin is exactly that, a struggle, and one which is ongoing in their lives.

It would be wrong to think that the sacrament of reconciliation is some sort of instant cure for these struggles, we of course need the grace received in the sacrament but grace builds on nature - it’s an ongoing process. If anything, the the fact that someone commits to keep coming back to confession time and again struggling with the same sin speaks profoundly of their deep desire for God’s help as well as the beauty of the sacrament as an expression of God’s limitless mercy. That doesn’t mean God does everything and we don’t have to do anything ourselves - there needs to be a desire or intention to avoid sin as well as concrete actions in support of the same.

At the same time though, human weakness (as well as the effects of ingrained habits and addictions) being what it is, we will always struggle - as St Paul puts it: "or I have the desire to do what is good, but I cannot carry it out. For I do not do the good I want to do, but the evil I do not want to do—this I keep on doing. God never abandons us in that struggle, He never rights us off as a lost cause provided we’re willing to seek His help and to keep committing (and recommitting) ourselves to Him. This is the story of salvation history. To my mind the greater risks are either acceptance of habitual sin as "normal_ - just one of those messy bits of life that will always be there - or despair, leading someone to think that they’re beyond God’s forgiveness.
 
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