How Close should the Connection be?

Paul is very seeker friendly - Connect first to their culture and bring Christ in.
1 Cor 9:19 For though I am free from all, I have made myself a servant to all, that I might win more of them.20 To the Jews I became as a Jew, in order to win Jews. To those under the law I became as one under the law (though not being myself under the law) that I might win those under the law. 21 To those outside the law I became as one outside the law (not being outside the law of God but under the law of Christ) that I might win those outside the law.
22 To the weak I became weak, that I might win the weak. I have become all things to all people, that by all means I might save some. 23 I do it all for the sake of the gospel, that I may share with them in its blessings.

The question is how close do we want to get? 
How can we bring Christ in after the connect?

A young lady went to Hong Kong to do missionary work among the addicts and triads member. See Jackie Pullinger Telling the story. There was a book about her work - Chasing the Dragon. She is the shining light in the darkness and God is glorified. 
Hudson Taylor adopted Chinese cultures, dressed, eat, lived like the Chinese to reach out to the Chinese.

I could not remember the name of the preacher I read years ago about him trying to preach to the slaves without success until he sold himself as a slave.

So, do we need to be become a prostitute to reach out to the prostitute? Do we need to be a thief to reach out to thieves? Do we need to be a drug addict to reach out to the drug addicts? Where is the boundaries? How can we live in their environment, adopting their cultures, without compromising the gospel - the very reason for us to reach out to them in the first place?

We need to use wisdom based on the Bible and guided constantly by the Holy Spirit as the danger and pressure for us to compromise is great. It is not for any to go to such extreme environment.

Can we become slave to save the slaves? There is nothing evil or prohibition for one to be a slave in the Bible.  However, becoming prostitute and thieves are prohibited in the Bible. Crossing the boundary that Bible set up is not wise but extremely dangerous. People in bondage cannot help those in bondage to break free. So, joining the prohibited vocations and sub-cultures to preach the gospel message is a lie and deception. We can go and experience in the sub-culture to understand and connect, but we cannot adopt those prohibited by the Bible. Because the pressure and temptations are high, it is better to do as a team. It is of God's grace and Jackie's watchfulness and alertness that she can go into the dangerous and dark cultures and be the shining light there.

Be wise. We are call to connect and shine with Christ and not to connect and become the same as them loosing our light.

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