I would agree that there is a lot of good advice here. Generally, *I* think I'm not creepy, but ultimately that's for the [] girl []gal []chick []woman [] babe [] nutcase (pick one) to determine.
And I like the DISmeet theory - the people I've met there are first class and people that I'd go out of my way for. It's also good for the ego to be the only guy in a room full o'women! But all by itself, that raises other issues.
Here's what I mean (and why I tread so gingerly on this whole subject). I would never date anyone I worked with. We all know why - if it gets sideways, then it just becomes awkward for everyone involved at work, and somebody will feel forced to find another job, either at the same workplace or elsewhere. That's just not fair.
Honestly, I feel the same thing here. Several years ago, I was in a Parrothead Group (Latitude 38, if anyone cares) in Northern California, and several people pulled me aside and said so-and-so wants you to ask her out. Well, I thought she was interesting and, against my better judgment I asked her out. Big mistake. Fun for a while, but ultimately we were not compatible. I broke it off, and this hurt her terribly. Ultimately going to club meetings became defined (for me) as going when she wasn't there, to spare each of us the uncomfortable moments. I don't know whether she gave me any consideration, but when she became a club officer I dropped out of the club. This was difficult for me, because I had a lot of other friends there I wouldn't see any more.
I sort of have the same impression about DISmeets. I really like the people I've met there, and I am tremendously cautious about changing that dynamic. This ain't about getting laid (sorry for being crass) - this is about building a long term relationship with someone with whom I have some commonalities, and for which I have set unbreakable criteria (not many - (1) they have to be monogamous; (2) they have to like, or at least tolerate, some of my passions. There aren't many others.). So I will move exceedingly slowly to make sure the important pieces are present. If they aren't and I move too soon, I risk getting into a situation like I describe above (if it breaks up). The downside to this is that I move so slowly that sometimes she may feel I'm not interested at all.
It's hard enough to make friends somewhere, especially being new to the DC area (within the last two years, and after a 20-year absence) without throwing a lot of baggage all over them. I want to enjoy my DISmeets, and not end up trying to decide if I will go because "Ms. So-and-so" won't be there.
Does any of this make any sense? I sort of feel like this was stream of consciousness. Puddle of consciousness? I hope you get it.
Anyway, there is, to me, some of the same risk to tossing a PM out there. It's easy to immediately cross the line from 'acceptable' to 'creepy' by emailing, and trying to be witty to someone I don't know very well. Once crossed, it is difficult to go back.
I just wonder if anyone else feels the same way. Am I a nut job because I'm being too considerate of other people's feelings? Am I being too cautious? I can't tell. Either way, I spent a portion of my life thinking all about 'me' and it was very unrewarding. I decided when I regained the emotional connection with humanity I had when I was younger, it was in recognition of the way I was wired in the first place, and I wasn't going to let it go (despite cultural pressure). So, yeah, I'm sensitive. I ain't changin.' It is where my intuition is rooted. That's too valuable to lose.
Okay - I'll shut up now.
Opinions? Did I make sense? Am I speaking Klingon?
Qapla'!*
Mark
* success.
, I met online first, through a game. I don't find it strange at all, though other people have. 
I completely see where your confusion comes from!
)
