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.

Update

So....I haven't written in here in a while. There's a reason for that. I haven't felt the need. This is a venting blog, and I have either come to terms with things or I have found a person to vent to.
I do however want to update you on things going on.
In my house we had an interesting roommate...she moved in for about a month or so and right from the beginning wasn't sure of her permanence with us. She had stated to one friend that she wasn't sure if she would stay past June. So for the entire time she lived with us P.R. tried to find out if she planned to stay with us or not, because honestly, we needed to know. We shall call this roommate, Nomad, I think the name is fitting.
So P.R. and Nomad were locked in an everlasting battle of question and avoidance. Nomad turned out to be a liar too. I cannot reveal much detail about all of this because having the den as my bedroom I spent much time down there and never really interacted with Nomad. I have a pretty good sixth sense on when to avoid people, and an even sharper one on who to avoid. I have always gotten the "avoid" vibe from Nomad, long before she moved in.
Anyway, S.F.H.B. graduated and moved home and try as we might we were unable to find a new roommate to take her place. This meant that come June 1st we were all responsible for $100 more on rent. So, P.R. did the only thing she could do, she wrote a note to Nomad - we would have said something in person, but Nomad was rarely there. The note stated that when rent was due it would be $100 extra due to the lack of a fourth roommate. It also had a few housekeeping items on there. On Sunday night (May 24th) P.R. received her own note, Nomad informed her that she would be out by the 1st. So, instead of rent being $100 more for each of us, P.R. and I were now responsible for half each.
And I was leaving to go out of town that Wednesday. Therefore P.R. and I communicated via e-mail of what was going on. Nomad was completely gone by the evening of the 30th, our landlady is crazy - P.R. explained the situation to her and she wanted us to pay a new deposit when we signed the contract for June, but for me that would have been $1500 - I choose to eat in the month of June so that's not possible. She told us to hold off on rent until we meet to sign the contract (since I was out of town) so I haven't felt the financial blow of anything yet.
On the upside, we found two girls to move in. They can't move in until August though, however, they have moved in their stuff and offered to pay storage. P.R. and I are not about to turn down money. We are going to use it to offset the cost of utilities, since that's going to hurt our pockets in the same way rent well (and by that I mean we are paying half rather than quarter). We are meeting with the landlady tomorrow evening to "sign the contract" but hopefully she is letting us carry over the security deposit until August, when all four of us can sign a contract together. The way she was wanting us to do it was for P.R. and I to both pay the security deposit and we work it out later with the two new girls. I'm sorry, but I'm not a landlady, I don't want to work out the security deposit with them. What...have them pay their portion and when I get mine back pay them theirs? I'm sorry but it's too much work. Besides, I would feel more comfortable having all of us locked into a contract, that way what happened to us with Nomad can't happen again.
Anyway, oh and our washer broke. Landlady things she has fixed it, but it may flood again. Not looking forward to when that happens. Needless to say not quite as much laundry is getting washed in our household right now. We don't need the stress.
AND I've given up sugar...today is day one, so who knows, maybe by the end of the week I'll need this blog more than ever.