Questions about confronting someone about their sin

[Jaxb]

I have to confront someone about their sin. He is one of my friends and he goes to my church. Please pray that God will give me wisdom and discernment and pray that the other person will repent.

How do you go about confronting someone about their sin?

Suppose I ask the person if he committed it, and he confesses that he did commit it. What more can I say than just, "You need to repent. You need to stop that sinful practice."?

Suppose he says that he will repent, but does not actually repent. How would you respond to that?

Suppose he says that he is trying really hard to repent, but can't seem to do it. How would you respond to that?

I am part of a prayer group that meets occasionally. This prayer group consists of some people who do not attend my church. Would it be appropriate to ask the group to pray for me about confronting my friend about his sin? Would it be appropriate to mention the specific sin that he is committing? How should I respond if someone asks me about the specific sin that he is committing?

[Spartacus]

First, the relevant Scripture:
Matt 18:15-20
15 “If your brother or sister sins, go and point out their fault, just between the two of you. If they listen to you, you have won them over. 16 But if they will not listen, take one or two others along, so that ‘every matter may be established by the testimony of two or three witnesses.’ 17 If they still refuse to listen, tell it to the church; and if they refuse to listen even to the church, treat them as you would a pagan or a tax collector.
18 “Truly I tell you, whatever you bind on earth will be bound in heaven, and whatever you loose on earth will be loosed in heaven. 19 “Again, truly I tell you that if two of you on earth agree about anything they ask for, it will be done for them by my Father in heaven. 20 For where two or three gather in my name, there am I with them.”

Not saying that you should get ready to kick your friend out of the church, but there's wisdom in this: rather than gossiping behind his back, you go to him first as a sign of trust. Then, you can bring in other people whom you can both respect to observe and arbitrate.

If he says he's trying hard, then offer to help keep him accountable. Having another person know about and support you in your struggles (especially as opposed to trying to sweep it under the rug for the sake of appearances) can be very helpful-- or so goes my experience.

As for how to go about it, think about what sort of approach would work on you: if someone was to confront you about your sins, how might they go about it in such a way that you would listen?

[Jaxb]

First, the relevant Scripture:
Matt 18:15-20
15 “If your brother or sister sins, go and point out their fault, just between the two of you. If they listen to you, you have won them over. 16 But if they will not listen, take one or two others along, so that ‘every matter may be established by the testimony of two or three witnesses.’ 17 If they still refuse to listen, tell it to the church; and if they refuse to listen even to the church, treat them as you would a pagan or a tax collector.
18 “Truly I tell you, whatever you bind on earth will be bound in heaven, and whatever you loose on earth will be loosed in heaven. 19 “Again, truly I tell you that if two of you on earth agree about anything they ask for, it will be done for them by my Father in heaven. 20 For where two or three gather in my name, there am I with them.”

Not saying that you should get ready to kick your friend out of the church, but there's wisdom in this: rather than gossiping behind his back, you go to him first as a sign of trust. Then, you can bring in other people whom you can both respect to observe and arbitrate.

If he says he's trying hard, then offer to help keep him accountable. Having another person know about and support you in your struggles (especially as opposed to trying to sweep it under the rug for the sake of appearances) can be very helpful-- or so goes my experience.

As for how to go about it, think about what sort of approach would work on you: if someone was to confront you about your sins, how might they go about it in such a way that you would listen?

Thank you for your advice. Matt 18:15-20 is the way to go.

If someone had to confront me about my sin, I would want them to follow Matt.18:15-20 and be honest among other things.