Wing Man

I have decided (officially cause it's always been my unofficial stance) that being a Wing Man can't ever work. There were always the obvious reasons to me why it won't work. The Wing Man could fall for the love interest of their friend they are being the wing man for - I think people can follow that one.
This past weekend I have realized that being a wing man won't work for another reason. You build a relationship with the person whom you are trying to set your friend up with. I don't mean it in the above mentioned, you fall for the person, kind of way, but you build this friendship that you can't transfer over to your friend. Is this making sense? Here's the deal, my friend kind of likes this guy at church, let's call him the Socially Awkward Rebel, or S.A.R. I have no clue why I started to talk to S.A.R. but I did. He's completely random and I spent the first month knowing him just trying to figure out what he was talking about. When I found out that my friend liked him I thought I would try and help. You know, get to be better friends with him and then invite him to things where she would be, and maybe one day be able to set them up or something. I had not realized at the time that I was going against one of my cardinal rules. So I am friends with him now, and I still want them to get together, but I have run into a problem.
The problem is I don't know how to get him to transfer his attention to her and how to get her to know him well like I do. I felt for a while that it was working (at least the getting her to know him well part) but I realized this weekend that it's not working. Then last night, said friend and I were talking and she says, "Do you think that maybe S.A.R. wants to date you?" What? No. Impossible. First of all he knows I have a boyfriend, second of all I'm the buddy! So I tell her the first part, "Well, he knows about my boyfriend." Her response was that he also knows my boyfriend is leaving. I asked her why she would think that he would want to date me and she said that it was just interesting to her that he asked me who he should date. Which he did, about two weeks ago he randomly asked me who he should date. I wanted to say, "My friend" but then I felt like I shouldn't give that information out so easily. I asked him what kind of girl he was looking for and he said, "Not ex-hookers who have found God" So I was thinking he was just kidding, but then he brought it up again and I told him that maybe he shouldn't focus on who he should date, but rather ask a girl out, get to know her, ask her on the first date if she is an ex-hooker. Then from there, figure out who you want to date. He said that was too much effort so I told him that he should probably go for the ex-hookers then. He's never mentioned anything else about it, so I had kind of forgotten the situation.
I had S.A.R. and friend in the same room the other night, and both spoke to me but not to each other. Which bummed me out because how are they supposed to get together if they don't talk to each other? It's not like there were a lot of people around, there were three people in the room! I think that friend just got nervous and S.A.R. just doesn't even think about it.
Another problem could be that the more I get to know S.A.R. the more I think that maybe friend and him aren't compatible, I never thought they were, I hoped I would find something...but opposites attract. So, right now I'm just working off the fact that friend would be willing to date him. I think I just want to find someone that she would totally click with, I want her to be with someone because she really wants to be with someone right now. If things between her and S.A.R. aren't going to work out then I think I need to back off because I don't want to be caught in a social awkward situation.
I have to graduate from Wing Man to matchmaker. There is a difference. Wing Man figures out things about the interest that the person has chosen, a matchmaker makes the choice. They find someone that their friend will click with. So I am on the search for someone she will click with, I am matchmaker...not wing man.