Last week I solicited questions  from the readers of this site, looking for good ideas for future blog posts. I received almost 100 responses, many of which asked really good questions. In the coming weeks and months I will attempt to answer many of them. I begin today with this one: “How do you discern when to take something up with a person and when is it something to just let go (is it ever right to just “let it go”?).”
There are a couple of Scripture verses that seem especially and immediately applicable to this question. Proverbs 17:14 says, “The beginning of strife is like letting out water, so quit before the quarrel breaks out.” This tells me that there are some situations in which strife is unnecessary and even unhelpful. A couple of chapters later we read “Good sense makes one slow to anger, and it is his glory to overlook an offense” (Proverbs 19:11). Put these verses together and we realize that we are not required by God to confront a person every time he or she offends us. In fact, there are times when we should not confront a person. And honestly, if every person I have offended confronted me every time I sin against them in some way, I would be an awfully busy guy. There are times when the best course of action is to leave our offenses between the offender and God.
So now the question before us is this: when do we confront and when do we overlook? I am going to follow, roughly at least, the logic Chris Brauns uses in his excellent book Unpacking Forgiveness  (If you haven’t bought a copy of this book yet, you really ought to do so. It’s a wonderful guide for situations like this one).
Before you do anything else, you will want to examine yourself. You will want to see if there is some log in your eye that you have missed in all the fixation on the speck in your neighbor’s eye (Matthew 7:3-5). You will want to examine your motives to determine why it is that you may desire confrontation (or perhaps why you desire to avoid confrontation). Are you angry and seeking revenge? Do you harbor a grudge against the person and feel like you can only ease this burden by telling him of his offense against you? Will you only feel better after you inflict guilt upon him? As you focus on your own sin and on your motives, you may find that the desire to pursue confrontation fades in the light of God’s holiness and in the darkness of ungodly motives.
You have now established that your motives are pure and that you are not overlooking a similar sin in your own life. Now you will want to examine yourself to ensure that you are right in this matter. Have you looked for Scriptural principles to determine if you have truly been sinned against? Is there clear violation of a Scriptural principle here, or are you dealing with a gray area? If you find that this is a gray area where there is no clear definition of right or wrong, it may well be best to simply put the matter aside.
If you have passed through the first two filters and still believe this is an issue worthy of confrontation, you will want to consider just how important a matter this is. Are we dealing here with a matter of preference or a matter of objective right and wrong? Is this an issue that will have long-term ramifications or something that will not much matter one way or the other? Are you making dogma out of personal preference? If, upon examination, you determine that this matter is not of great importance or that it is more about preference than anything else, just let it go.
There are times that we sin in a way that is out of character for us. For example, you may be consistently punctual but then, one day, show up late for an important meeting. In such a case it would probably not be worth my while addressing this offense. However, if you are constantly showing up late for even the most important meetings, this may be a matter I should address with you. It may still not be an area of sin (perhaps traffic is wildly unpredictable or you have a young child who is waking you up all night long, making it difficult for you to spring out of bed). Either way, we often do better to confront patterns of sin or offense than isolated incidents (though, obviously, with more egregious offenses we may need to confront them immediately).
Before approaching the person who has offended you, ensure that you are being sensitive to his or her unique situation. There may be stresses or strains in that person’s life that are causing him or her to act out in ways that are atypical. In such a situation you are not excusing the person’s sin but, rather, understanding that difficult times can cause even the finest Christian to act out in ways that are unusual for him. Adding the burden of confrontation may not be the wise or sensitive thing to do at that moment.
Whether or not you choose to confront may well also depend on your relationship to the person who has offended you. There are some relationships that are more likely to bring about good results. For example, only with great hesitation would I ever directly confront a woman and even then only if she was a good friend. However, I have friends who are eager and willing to hear of sin in their lives and who would appreciate such counsel or loving confrontation.
It may be valuable to seek the counsel of other mature Christians before pursuing confrontation. You will want to ensure that this is not simply an opportunity to gossip and vent, after which you will feel better and let the matter drop. But discreetly seeking wise counsel may be a very good way of “error-checking” your assessment of the previous four steps.
If, after such an assessment of your own heart, the offender, and the offense, you still feel confrontation is necessary, you will want to pursue forgiveness and reconciliation in the way Jesus outlines in Matthew 18.
However, far more often than not, I think you will find it is wise to let the matter go. And here you will need to release your pride and outrage. You will need to be willing to let the matter well and truly drop, not telling others about it and not letting it fill your mind and outrage your heart. It is the glory of a man to overlook an offense; it is a foolish and prideful man who feels every little offense is worthy of confrontation.