When you go to church and church related events, most people put on their best mask so no one will see what they really are. Or in some cases, church-goers genuinely are very clean people with little visible sin in their lives. That is because church is all about trying to fix you up enough that you are presentable to God. To make you good enough to deserve to talk to Him, when in reality you have already been made perfect. Christians warn about being associated with the wrong kind of people in nearly every youth service I have ever heard! I find this incredibly ignorant... First of all if every one that knows the gospel only kept to themselves about it, how would the good news travel? How could we bring peace to others? Secondly, in Matthew 11:19 Christ is called a FRIEND of sinners. He isn't referred to here as someone who associates with sinners, no, he is referred to as their FRIEND. To me being a friend is a lot more than just caring about someone. You hang out together, have fun together, laugh and cry together. Jesus was said to eat and drink with these sinners. Not cool-aid either, Jesus drank wine! Christianity is more moral than Christ!
Should you go out and get trashed, snort crack off a stripper, and then have your way with any woman in town? If I have to answer this for you then you need more help than I can provide. Obviously that would be stupid. That isn't what Christ was doing. However, he was FRIENDS with these people. I am willing to bet (Oh no, did I just mention gambling? Forgive me God!) that if Christ had a Facebook, his friends list would contain thousands of the earth's "scummiest" people in the eyes of the religious. And if he had Myspace, his top 8 would include the likes of Dirty Steve, Drunken Bob, and Anthony Kiedis. It sure as heck wouldn't have the pope, John Hagee or Kirk Cameron. Does he love them? Yes. Would he hang out with them and drink a couple glasses of wine with them? No, because they would think they were hurting God's feelings by enjoying life.
Don't avoid people just because they seem to not care about the choices they make. Some of the best people I know drink, smoke pot, eat more than the suggested serving size, and even roll through stop signs. You will be surprised at how much more they will receive the message of pure grace.
