How can I lovingly rebuke a friend about issues I have brought up in the past? I’m afraid of sounding pushy or something.
There is not magic way to make people react well to confrontation. That is one of many reasons that the main question about confronting someone is: do I have any right to be opening my mouth about this? There are a few situations in which you definitely do.
If the person is crossing a boundary you have set. Luke 17:3 says that if someone sins against you, you should rebuke them. That “against you” is a very key point. If someone is acting in a way that directly negatively affects you, then it is important for you, them, and your relationship that you have the courage to confront them on that.
If you are in a mentor/pastor role. If someone has given you authority to speak into their life, then you should take that seriously and speak up when you have to. That is a burden of leadership, not the fun part. The way you earn that authority is by humbly serving people consistently.
A life or death situation. If someone is going to put themselves in imminent danger, then you might have to speak up.
If your situation falls into one of those categories (most likely the first) then you should just be direct, firm, and loving. It is not a negotiation, you are telling them how you want things to be. But you are not judging on them, you are just letting them know that the way things are now is not working for you.
Other than those situations, you are pretty much always better off keeping it to yourself. Pointing out their faults to people who didn’t ask is a pretty annoying proposition. It hurts relationships. It hurts your witness with anybody who might see you as a busybody know-it-all. It is largely a no win proposition.
It sucks to see the people around you doing things that you know will end badly, but it isn’t always your role to speak up about it. In fact, there is a pretty narrow set of circumstances where you should. In Matthew 7, Jesus talks about the danger of pointing out other people’s flaws when we all have our own problems. Without a prayerful, careful, mature approach, going around rebuking left and right is a sure fire way to make sure that no one wants to hear your opinion.
By contrast, living your walk out humbly and with a non judgmental servant’s heart will set you up to be the person someone goes to when they know that they need some help.
-Matt from The Bridge