The gospels regularly use the word 'sinners' in a way to indicated those known, in a close-knit society where everyone in torn knew what everyone else was up to, those known to be notorious breakers of commandments. Jesus is well known to be a friend of these kind of people. So, what sort of people does Jesus spend his time with? Whores, Criminals, and Terrorists. That's it. Firstly, whores. Jesus associates with women known to be sexually immoral. John 4 has Jesus talking with a Samaritan woman who has remarried 5 times and now is with a man not her husband. The woman who comes and washes Jesus' feet with her tears and anoints them in Luke 7 is known to be a 'sinner', i.e. a publicly known sinner, almost certainly on the basis of sexual immorality. In Luke 5 Levi (or Matthew) hosts a big party, and he's a tax-collector, a group of Jewish collaborators with Roman rule who collect taxes, basically on an auction system, and pay them on to Roman equites, and keep whatever they can, so they're running around with a protectionist racket with stand-over men and basically they're the Judean answer to the Mafia. Likewise Zaccheus in Luke 19 is a 'chief tax-gatherer' and so some kind of made-man or don, who collects taxes from his hitmen and pays it onto the Romans. Matthew 19 identifies Jesus as 'a friend of tax collectors and sinners', meaning everybody knew who Jesus hung out with. Jesus also hung around terrorists. Mark 3:18 identifies one of Jesus' twelve disciples as 'Simon the Zealot', that is one of a group of political extremists within Judea at the time who were willing to use violence and had the stated intention of a violent overthrow of the Roman government in order to restore an Israelite state, as in the time of the Maccabees. Jesus took one of those guys into his trusted 12, a guy who probably had quite a beard and slept with a knife under his pillow.
This is the kind of guy Jesus is. He hangs out with them, befriends with them, welcomes them into his closest circles. He doesn't invite them to join a program, tell them to come and talk to him when they're not hung-over, or anything like that. He turns up at their parties, invites them to his parties, and generally they have a great time together.
And when Jesus is on trial, despite his reputation as a drunkard, a glutton, and all the guilt by association (You can imagine, "Jesus, did you ever lend a SIM-card to Simon, because he's on file as a terrorist"; "Jesus, did you ever smuggle any liquids through customs?", this to the guy who turned massive amounts of water into high-quality wine), despite all this they cannot pin Jesus for a single crime. They have to whip up some perjurious witnesses to testify to Jesus' talking about the temple's destruction, badly misquoting Jesus (it's a fix-up from the start), push him into a blasphemous claim about divinity (which Jesus' can make and isn't blasphemous because it's true), and mis-represent his teaching to Pilate (to whom he plainly tells, 'My kingdom is not of this world', making abundantly clear how radically different his teaching is). But, in the end, they can't pin him for a single thing, and Pilate has to conclude, "Why, what evil has this man done? I have found in Him no guilt demanding death" (Luke 23:22).
Jesus is Sinless.
I belabour this point to get to another one. What does it mean to imitate Jesus, and to pursue a mission like Jesus'?
John 17:15 and the verses surrounding it put out a tension for Christians: that we are in the world, but not of the world. We are engaged, but to be protected from the evil one. 1 Thess 5:22 reads "Abstain from every form of evil". Likewise 1 Tim 6:11 talks about fleeing the temptation to riches. 1 Tim 3:7 lays out the qualities for an elder, including "it is necessary also to have a good testimony from the outsiders, so that he might not fall into disgrace (reproach), even the snare of the devil".
Now let me ask the radical question, Are you willing to lose your 'ministry' for the sake of Christ?
If you've been around long enough in Christian circles, you will hear tragic stories of Christians in ministry who have lost it. Some, through scandalous sin are rightly deposed and it's truly a tragedy. Others, through scandalous rumour and accusation, unsubstantiated, are asked to leave their positions.
Let me make some points:
1. It's right to avoid sin, no question about it.
2. It's also right to (a) avoid certain temptations, (b) put in place safeguards for one's reputation. For example, it's a great idea to run filtering software, or better yet reporting software, on your computer, to avoid temptations of internet pornography. This is a good thing. Likewise, it's wise not to spend time alone with members of the opposite sex in private environments.
3. It's wrong to avoid 'sinners', including in contexts where they are sinning, except when your presence would constitute a sin itself. Examples: (1) It's not good to sit down and watch a porn film with your friend who is a sex addict. That's not helping, and it's not right for you. (2) It is fine to be at the pub with your friend who gets drunk, provided that you aren't getting drunk too. That's presence without sin.
4. The solution to temptation is not dis-engagement. Consider this: We often have an image of Jesus that is supra-, and therefore sub-, human. We think of Jesus just cruising through life like some kind of moral superman, tempted, but not really, by sin. Is this the picture of the scriptures? No. Hebrews 4:15 describes Jesus as "tempted in every respect like us, without sin". Jesus was a single man throughout his life, and he hung out with whores. He was sorely tempted, beyond what you and I can imagine. Jesus went to wild parties with drunkards and gluttons. He was not a drunkard. Jesus lived as an itinerant with little wealth, in the company of some who were accustomed to use violence as their means of living. He was sorely tempted. The solution to temptation is not retreat, but holiness. It's walking real close to Jesus, talking to him, knowing the scriptures, (consider Jesus' temptation right at the start of his ministry). It's not trying to do things alone, but keeping close to brothers and sisters, confessing sins and keeping one another close to Jesus. The answer to temptation is not avoidance, it's Jesus. It's innocence coupled with wisdom, not naivety. That's what Jesus is saying in Matthew 10:16, "Behold I am sending you out as sheep in the midst of wolves, so be as wise as serpents and innocent as doves". he's sending them out into a world which will eat them alive, and he tells them - play it smart, and stay holy. He's not saying, 'play it dumb, and stay home with the tv off'.
5. Lastly, you might have to sacrifice 'your ministry', to be a part of Jesus' mission. If you start spending time at the pub, visiting the home of pot-heads, befriending hookers, then religious people are going to get mighty worried about you. They're going to get mighty worried about your reputation, and the reputation of your denomination, and they're going to quote 1 Tim 3:7 at you. And that might be okay, if you're being faithful to Jesus. We read 1 Tim 3:7 with what I will call Pharisee's glasses - we wonder what the good people will think. Jesus' reputation with the Pharisees is mud. But his reputation with 'the outsiders', with whores, terrorists, and thugs, is really 'good', even 'beautiful'. He's their friend, he's partying with them, and he's loving them, which includes him saying, like some kind of broken record, 'The Kingdom of God is at hand, Repent and Believe the Good News'.