A Gospel Chat leaving me with more questions than answers

I’d like to think more about something that happened this evening… any comments gratefully received…

Me and a mate went for a drink after work, catching up about the summer… at the end of our catch up, the pub was getting busy (noisy) so we headed outside to pray… found some seats in a quiet spot… off the street… We're praying and we're interrupted by a homeless guy, who wants to pray with us… we invite him, and he'd like us to pray for him, that he would stay off drugs (he was currently off drugs)… we prayed for him, attempting to get the Gospel in as we did, and he prayed too… He then asks "why did Jesus die for me?"… We explain, attempting to make it as simple as possible… The guy said that he prays each night… We get talking about whether he had somewhere to stay that night… and he didn’t… he needed money to stay in a hostel (I still don’t quite understand how homeless shelters charge for people to stay - maybe they don't - hence this post)… he then asks if we could help him out…

A number of things run through my head…
Has this praying and chat just been for him to get to this question… is that a realistic thing to think? is it me being sinfully judgemental? Maybe bit of both?

What do we do in those situations?

It happens a fair bit, walking past a homeless guy, and they ask for money… sometimes if there's somewhere nearby, I might offer to buy them some food or a drink… but the response is sometimes "I need money so I can stay in a hostel"… how should we balance Christian giving and charity, when we're not totally sure how the money will be used… should we be giving money if it's only going to be used on drugs or something, and not for a hostel? Have I not let the Gospel transform my thinking, or am I right to be suspicious?

Of course, theirs, as much as the top City professional going home to a large house in the country, only has one ultimate need, and that is to come to know Jesus and the forgiveness he offers at the Cross… certainly the priority in our conversation with this man.

As we leave him (my mate giving him some money) we hand him a copy of Mark's Gospel… we've only got an ESV… I think to myself: that's not exactly your easy-going translation (has our desire for accuracy made a less accessible Gospel? Can I even dare ask that????), but maybe coz it's narrative it'll be ok… then I had Acts 8:30-31 ringing in my ears. That then led me on to thinking: he needs to come to church… but I couldn't help thinking: would he feel comfortable, would he understand the sermon when basically it's aimed at graduates… and I just wasn't sure… and that's where I'm left… a bit tied up in my thoughts… (Greg is very much missing his sounding board)

An encouragement from Calvin

"whenever we are troubled at the small number of those who believe, let us counter that by calling to mind that none grasp the mysteries of God save those to whom it is given"