If we're going to talk about engaging the culture without entertaining it, like Jesus did, then we have to start by throwing off some of the myths and heavy burdens that Christianity has bought into for far too long about just what the tough places in this world mean.
There are many Christians who believe they should never step foot in a bar. They wouldn't be caught dead in a brothel. There's no way they're going to a Pride parade. Too many Christians wouldn't even go to the hospital with a drug addict. Heck, we aren't even visiting the mentally ill without addictions.
What I'm saying is - Christianity has drawn its lines.
And we have justified those lines by drawing them even thicker with temptation. We can't go anywhere where we might be tempted into sin. Or might be caught up in it against our will. (Like, for example, if the police were to raid the drug house you're visiting a struggling brother in while you're there and you accidentally go to jail for a bit because of your mere presence there.)
We put all kinds of language around this. "Living above reproach," which is fancy language for, "What would other people say if they knew I was in a place like this?" "Guarding our hearts," which is fancy language for, "My own dirt might get exposed in a broken place." We could go on and on. The point is - we have drawn our lines and declared our justifications.
But what it really boils down to is...we don't like unclean places. And we want to feel "safe."
And these lines and justifications are so engrained in most of us that we can't even fathom going into the broken places because these voices just start shouting really loudly in our heads. We have all of the rationales, and when someone suggests that we go into the broken places, we're sure that God wouldn't want us to do that. We're certain that God's the one who put up these "hedges of protection."
In fact, if you look at the Scripture, God says just the opposite. A lot.
Jesus Himself said that it's not the healthy who need a doctor, but the sick. And even though we live in an age where we go to the doctor, the majority of human history has had doctors who come to you. So Jesus could not fathom a doctor who would not go where the sick were. It's why He had lunch with so many sinners.
Even beyond that, Jesus also said that it's not what is outside of you that makes you unclean, but what is inside you. What gets into your heart. What you let become part of the core of your soul. He was talking about food and about washing hands and so forth, but the truth is the same for the places we go in this world. There is nothing inherently unclean about walking into a bar; it doesn't sully your soul just to be there. If you let the culture get into you and find yourself drinking too much alcohol, that's a problem. But just being there is the same principle - it's not where you are that makes you unclean; it's what your heart is doing there. (So, of course, if your heart is loving one another there, then it does not make you unclean.)
And then, God lowered a sheet from heaven to show Peter that he could eat anything in this world - even the stuff that used to be unclean. This was because Peter needed to go into places that didn't practice the same kosher diet that the Jews did, and it was a point of possible tension between Peter and those he was going to share the message with. If he went into these places and pretended that he was so distinct from them, so far separate that they couldn't even share the same table, no one would ever hear the Good News when he spoke it. The same is true for us. If we keep trying to tell the world that we're so distinct from them that we can't even eat together - that we can't be in the same spaces around the same places - they aren't going to care what we have to say. They won't hear because they won't be listening.
If this is the example God has given us and Jesus Himself has set, then we must break out of our rationalizing mindset and realize that no, there is nowhere in this world that we can't go. More than that, there is nowhere in this world that God wouldn't have us go if there is someone there who needs His love.
That's step one.
(And yes, of course, it is important to understand our limitations as broken, fallen human beings. If you can't personally go to a bar without succumbing to the temptation of an excess of alcohol, then don't go to a bar. Don't go to places on the outside that you know you are susceptible to letting get inside your heart/soul.)