I've been a volunteer for Big Brothers Big Sisters for 3 years, all with the same boy (now 10 years old), whom I'm going to call E. In general, E and I have quite different interests. While at first this might seem to be a poor match, it has led to eye opening experiences for both of us. He's very different than I was at 10, but we stumble upon things that both of us really enjoy with increasing frequency.
I have been waiting for the right time to try introducing him to RPGs, and have tried to laying some groundwork over time, seeing what other activities he liked that I could use as an introduction. We have played out big battles on the floor with my gaming miniatures, making up rules as we went along, randomly using dice for movement and combat. E refers to this as "our game"; it's sort of a wargamer version of CalvinBall. Last year for Christmas I bought Nerf swords, and we and ran around in the woodsattacking trees, bushes, each other, basically anything that was slow enough not to get out of our way as we fought off hordes of goblins and dragons. He's has a passion for reading, and both of us love taking trips to the library where we go home with more than we can reasonably read in the 2 week loan period.
Other things have not gone quite so well-the copy of The Hobbit I bought for his 9th birthday is still unread, and various fantasy movies have been turned off in the middle in favor of Rock Band or other games on the Wii. A day trip to one of the caves in the area turned into a painful experience when he realized the tour group was, literally, a captive audience for his antics.
But back to the more recent past. We were in a used book shop on a rainy day a few weeks ago, I was looking at graphic novels and sf novels, he was looking at the young adult books. E says to me out of the blue "Hey, when can we go out in the park and fight monsters again? Like in the myths?" referring to a book of Greek mythology he was reading. I smiled inside, seeing my chance to introduce him to RPGs. "Well, I think I know what we can do... Let's go home and I'll show you." 30 minutes later (after lots of "What are we going to do? Huh? Tell me!"), we were at my dining room table, with pencils, graph paper, dice, a copy of Labyrinth Lord, Stonehell Dungeon, my old copy of the D&D Moldvey Basic set, and we were creating his first character.
To be continued...
Listening to: Candlemass