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How should we confess?
Do we go to detail such as the event that the sin occured or just a generic listing of the sins we have committed and being open to the questions the Priest may ask on one that may standout?
or do we go,
I have done Sin X numerously and can't quite stop myself from doing it.
Sin Y I have done once and I think I will never do it again...
I think both of the models in the question are acceptable. There are really two important points to make here:
1. The success of confession does not depend on the number of words you use to confess nor on the amount of time you spend in confession. A long confession is not better than a short one. It DOES depend ont he sincerity and the depth of your repentance, for after, that is the whole point of confession. One might be quite sincere in regretting sin, yet only state that sin in a few words in confession. On the other hand, another person might spend hours telling stories in confession without ever feeling any deep regret about their actions.
2. You should only say those details that are necessary for you to feel that you have exposed the sin before God and your confession sufficiently. Don't let yourself leave confession thinking, "I wonder if I really confessed the sin, or if in fact I just covered it up so he wouldn't understand what I was saying?" An important part of confession is total honesty. Again, this is not to say that one should multiply their words; only that they should choose their words effectively to communicate the sin in all its stark ugliness, for this is the truth: sin is ugly.
If your confession Father feels that you are having trouble getting something out, he may gently probe with questions to encourage you in the direction of honesty. If he doesn't, there is nothing wrong with asking him to!