5For even when we came into Macedonia our flesh had no rest, but we were afflicted on every side: conflicts without, fears within. 6But God, who comforts the depressed, comforted us by the coming of Titus; 7and not only by his coming, but also by the comfort with which he was comforted in you, as he reported to us your longing, your mourning, your zeal for me; so that I rejoiced even more. 8For though I caused you sorrow by my letter, I do not regret it; though I did regret it—for I see that that letter caused you sorrow, though only for a while— 9I now rejoice, not that you were made sorrowful, but that you were made sorrowful to the point of repentance; for you were made sorrowful according to the will of God, so that you might not suffer loss in anything through us.
Paul reminds the Corinthians of the many conflicts of persecution he suffered because of his love for them. In this intensely autobiographical section of the letter, he conveys to them his joy in hearing from Titus about their “longing,” “mourning,” and “zeal” for him. This brought Paul great comfort, which as we have pointed out before has the sense of helping Paul endure his struggles. He is so glad that his hard correction in a previous letter did not drive a wedge between them and him.
Interestingly, there was a moment of regret in sending it, but now he is overwhelmed with joy because he sees the result: they repented of their behavior. The apostle Paul was not immune to what we all struggle with, the second thoughts about our efforts to confront people about their sin. We fear that people will not accept our admonition and instead reject us. Or we can fear that we will come across as judgmental or be seen as having a condemning spirit (see 2 Cor. 7:3). But we are commanded in Scripture:
Brethren, even if anyone is caught in any trespass, you who are spiritual, restore such a one in a spirit of gentleness; each one looking to yourself, so that you too will not be tempted. (Gal. 6:1)
Yes, confronting someone will make him uncomfortable—it is never easy for a person to own up to his or her sin, much less hear about it from someone else. This is one of the burdens of fellowship, and we must do it. But our attitude must be right, “in a spirit of gentleness,” not condemning—and believing the person will work through his discomfort over being confronted for the sin, and in the end repent of it. Nothing brings greater joy than one sinner who repents; this is what motivates us to work past our own discomfort in confronting people and holding them accountable. In the end, we all win!
Lord, help me get past my own discomfort to help my brother confront his sin.

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