I found both sides of this exhortation from Kevin DeYoung challenging and helpful:
Jesus never apologized for getting on the inside with outsiders. It was his mission. What kind of doctor refuses to see patients? What kind of farmer refuses to get his hands dirty? What kind of church has no place for sinners?
People reviled Jesus. They called him a glutton and a drunkard, a friend of tax collectors and sinners. Have you ever been called names like this? Have I? Do we fear contamination from the world more than we have confidence in Christ’s power to cleanse?
Of course, I’m not encouraging people with drinking problems to go hang out in bars. I don’t expect new Christians to keep all their same friends who lead them into the same temptations. I’m not saying that if you really want to be relevant you have to watch sleazy movies so you can talk about them with the sinners in our lives. We need to use wisdom.
And we also need guts. We must not think of relationships with non-Christians primarily as dangers but as opportunities. Do we go out into the world hoping for conversion or expecting contamination?
Greater is he that is in us than he that is in the world (1 John 4:4). Do we believe that?
The gospel–if we are talking about the true gospel–works through repentance and relationships. We need both. Jesus had relationships with sinners and tax collectors. And through those relationships what did he call them to do? He didn’t say call them to self-expression, or invite them to despise religious people, or summon them to eat, drink, and be merry (in our language: eat, drink, and be tolerant). He called them to repentance. One commentator says, “Jesus neither condoned sin, left people in their sin, nor communicated any disdain for sinners.” Jesus was not passive, just waiting for people to get their act together. And neither was he passive about confronting sin.
No one in the history of the world has been more inclusive of the broken hearted than Jesus. And no one has been more intolerant of the impenitent. A friend of sinners and no friend of sin.