I've never really considered myself a part of the OSR, or any old school movement. When I decided that I wanted to run this game online I started looking around for a system to use. Free was the first consideration. This was a game for someone who might not actually even like it. I didn't want her to go out and spend a bunch of money on a game, or hobby, that it might turn out that she wouldn't like. Simplicity was the next consideration. I am, at heart, a pretty rules light kind of guy these days, and games with a lot of crunch really aren't really my thing anymore. Even with those two considerations, that still leaves a lot of games as contenders.
Eventually I narrowed it down, and I ended up settling on Swords & Wizardry as the game to use. I liked the clearer explanation of the rules from the original (and better organization). I had hoped that it would make it easier on someone who had never gamed before to be able to get into the rules. We start with Whitebox, because of all of the available versions of the game, this was the simplest of them. It seemed a good starting point. The game clicked for all of us, and the mechanics were mostly easy enough to understand for her as well. She had a few difficulties understanding some of the finer points that those of us in the group who were more experienced with gaming had come to grips with long ago, but some further explanations (and none of us being afraid to look stupid helped a lot) smoothed things out eventually. However, one of the things that seemed to help her out the most was when I reccomended that she read Matt Finch's (that's the creator of Swords & Wizardry) Quick Primer to Old School Gaming. I don't agree with all of it, and I certainly never played all of the ways that are talked about in it, but it is definitely a great resource for understanding this style of play, and it helped her to better understand a lot of the things that already made sense to the rest of us.
Over time everyone fell into their characters and the idiosyncrasies of my style of GMing, and we all had a lot of fun. Battle were fought. Scars were earned. Narrow escapes were made. Along the way we even playtested a few things, and my friend wrote her first adventure and tried her hand at GMing herself. Really, not so bad for about seven months of gaming.
