I haven't touched any flavor of D&D in a number of years, but I figured that I'd throw in for this one because it would be interesting to revisit some memories.
I was introduced to D&D - specifically the Basic set - by my next door neighbor and childhood best friend, Richie. He had gotten the boxed set for Christmas (I want to say 1979 or so), but he was a couple of years younger than me and couldn't make heads or tails of it. I had heard of the game, even seen it a couple of times in the used science fiction bookstore my dad used to take me to called The Magic Door. He had never been willing to shell out the cash for the game, but I did have some experience with a number of microgames that he had bought me. So when Richie asked me to help him figure out how to play, I figured (in my 8 or 9 year old way) that I had a handle on it.
We were pretty wrong, and it took until I got my own set when I was 10 or 11 to actually figure out how to play and what was going on. In the interim, we drew on the maps and tried to play it like a boardgame. We "played" through Keep on the Borderlands over and over again. I don't remember anything about what characters we used. In all, it was a pretty abortive attempt by a 9 and a 7 year old at trying to puzzle out Basic D&D on our own.