Although I don’t think of my regular group as strangers, I did meet them all through my regular game. But in the last month I’ve played in six different games with people I had never met before. Thankfully the people were all cool, friendly, and well adjusted. In fact, this past weekend I played in a game run by @gamefiend (of the popular At Will blog) and I had only met him two weeks ago while playing Pandemic!
There are a lot of advantages to playing with new people. I’ve learned new techniques for role-playing, tips for running characters, cool race/class/power combos, and I have better understanding of the rules from gaming through unfamiliar scenarios. I also go to make contacts in the game industry and met others bloggers that have already helped me out. Gaming with an unfamiliar group is a like skill challenge: it’s work xp if you succeed, and if it fails, maybe you get into a fight, but noone dies.
I find there is always risk and fear when meeting new people. I have not always clicked with a random group. In my experience this happens when there is a big disparity in age between yourself and the other players. It’s also tough when the other people already all know each other–it takes awhile to become part of an established group, and you won’t have that time if it’s a one-shot. Fortunately, this is a whole lot better than dating: first of all you already have something in common (D&D), and secondly, there’s no fear of “gamer shame” (that tingle of embarrassment some people have when telling non-gamers about their hobby).
In conclusion, I don’t have a lot of advice about how to meet new people game with (conventions, gamedays, the friendly local professional game store, the internet), but I highly suggest that you do. It’s a great way to learn new aspects of the hobby and make new friends.