In Matthew 18, the people asking the questions (and Jesus) were Semites/Jews. Their background, worldview, and psychology (self and other awareness) were not the same as ours. The backdrop for trespass and “aught against” was the Mosaic Law, and their psychology was corporate/others-centered, not individualistic. If we import our western values and sensibilities into the text, we will misunderstand, and misapply it, with resulting great negative consequences.
For them, trespass and “aught against” meant:
- A just complaint (note: not a “perceived” one!)
- Having suffered actual damage or loss, a legal charge
- Suffering loss because of theft
- Anything causing the community to suffer loss in substance or reputation
Here’s how we typically interpret and apply this passage:
- So and so said something about me behind my back, they owe me an apology; I am not going to receive any thing from them until they apologize
- So and so hurt my feelings, they owe me . . .
- So and so caused me pain, they owe me . . .
- So and so is mad at me
- So and so doesn’t like me
- So and so is offended with me/I’m offended at so and so
These are all illegitimate readings into the text. The original hearers (and Speaker) could not have understood it so.  Individual consciousness and psychological self-awareness, as we understand them, simply did not exist in their time and culture.
The context is not about personal feelings being hurt. The context is the disruption of community due to actual, objective loss in a legal sense (against the backdrop of the Mosaic Law). The passage deals with the “biggies:” major offenses, Ten Commandment issues such as theft, lying, slander, libel,  fraud, cheating, adultery, etc. This covers basically anything that causes my brother (and by association, the community) objective loss in substance or reputation. In our culture the closest equivalence would be civil or criminal offenses, not petty psychological disappointments. What’s the point?
The Mt. 18 procedure applies to circumstances involving objective damage, actual trespasses/sins, civil wrongs in the community, not perceived psychological wounds and offenses, i.e.: “you hurt me.”
Some interpersonal offenses can, and should be handled simply by forgiving! There’s no need to bring every matter up in a formal Mt. 18 sense!  The Mt. 18 process is for impasse on major sins considered in our culture as illegalities: that is, circumstances where an individual has suffered measurable loss of some sort.  This passage has nothing to do with the hurts and misunderstandings common to life, or holding to and articulating a private opinion on a topic.
Our Western culture and society (a self-esteem, self-awareness, ego/individualistic, need-centered culture) is entirely too inwardly focused and inwardly fragile. Applying the Scriptures onto our backdrop, and reading our psychological worldview into this, or any other text, is illegitimate. It’s called eisegesis: reading into the text.
Now, it may be, and is, smart to resolve interpersonal issues as quickly and directly as possible. But this passage cannot be used on individuals as a mandatory grid through which every issue that pops up in a community must pass in order to legitimize some perceived grievance or complaint. Why does application of Mt. 18 “break down” in our individual, psychological, need-based culture?
Mt. 18 cannot function in a climate of self-perceived psychological need. It was never designed to.
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 We must first determine what a verse meant to the speaker/author and hearers before we attempt to apply it to ourselves.
 Loss is not limited to material goods. In an honor/shame society such as Christ’s, the loss of reputation would be far more grievous than loss of material goods. An individual’s loss of reputation was legally and morally equivalent with loss of reputation of the group. Our culture’s value system focuses more on material goods than reputation. Slander and libel are illegalities in our judicial system. However, it’s almost impossible to get a conviction in our “free speech” culture. Scriptural admonitions such as, “when one suffers, we all suffer,” have more kingdom implication than most Western churches would acknowledge.
 See Proverbs 17:9, 16:20, 25:2, 10:12.
 Some psychologically minded individuals might argue that psychological pain and damage is real loss, even in a civil or tort sense. While this is true in our culture, the original authors and hearers of Scripture would have thought no such thing; therefore, we cannot read it into the text.