Paul sets a pattern of pastoral ministry for Timothy that includes “teach, correct, rebuke and encourage” from the word of God. So there will be times when we are to lovingly and encouragingly rebuke people’s actions and decisions.
Sometimes, we know those people and we can be quite confident they will take it well – some people I know love a good rebuke!
But if you’re not sure how someone’s going to take it, it’s probably better starting with that conversation before you raise the sin with them… the conversation that goes like, “Hey, how do you reckon you’d respond if I challenged you from the bible about an area of your life?”
Now, sure… that’s going to ruffle some feathers. But it’s still an hypothetical discussion. You can still talk about it and talk about how God shapes us and challenges us through other people spurring us towards Christlikeness.
If that conversation goes well, there’s a much better chance the following conversation will go well too. If that conversation goes bad… well… you’ve raised an even deeper issue to work through. :)