The most embarrassing moment I had as a DM came the Christmas of 1979. I was 15-years-old, and I had only started playing the game 15 weeks before. When it came around that my parents asked me what I wanted that year, I was definite about wanting the new AD&D books (which had only become available in my part of the world that Autumn) and dice. Which they, astoundingly, got for me. A nice new copy of the DMG and the Player’s Handbook (both of which I still own) and a Monster Manual. I also still have the original 20-sided and 4-sided that came that Christmas.
I had been able to read parts of the books before, but having my own I quickly disappeared from the world all through Christmas Day doing nothing but reading, both going to bed and then starting early in the A.M. (my family always opened gifts Christmas Eve). But then after dinner my parents insisted on playing this new game - they did not understand why I was keeping it to myself.
It helps to remember at the time that there was no media about the game - the first time my parents ever heard about the game was from me, and they had no idea. But you try explaining D&D in an age when there were no home computers and no video games (both Donkey Kong and Pacman came out in 1980, so that tells you what I was up against). Nevertheless, I agreed.
As an aside, my parents are terribly straight, normal people, upper middle class, educated, mildly paranoid about crime and obsequiously reticent about anything - or anyone - that's different. Please keep this in mind.
Well, they didn't do so bad with rolling up characters. It had to be very simple, I hadn't been a DM before, and I'd only played a dozen times. I'd only played the AD&D system for a month. So I kept it simple: my parents rolled up two fighters and my older sister rolled a cleric.
I started them off in a dungeon and the wheels went off the wagon immediately.
To start with, they just couldn't grasp the concept of no board and no pieces. Even my friends played without miniatures (the push for little lead figurines had not yet hit the game where we were), and I was used to everything being in our heads - combat included, of course. Unfortunately, my mother could not picture any of this in her head. She does have an unfortunate habit of losing her place when it comes to movies with more than six characters, as she can't remember what Bad Guy B is doing at the warehouse in Scene 23 ... so this meant my often repeating descriptions which, let's face it, I wasn't very good at giving since I was young, ignorant and inexperienced.
When they came to a door that was jammed shut, with all characters failing to roll the die to open it, my father the engineer borrowed a ten-foot-pole from my mother (everyone had ten-foot-poles in those days, it was the style at the time) and with his two ten foot poles proceeded to lever the door open. He gave me a complicated description - complete with diagram - on how this was possible and how the door would not be able to resist the force the two poles could apply, if the poles really were two inches thick and made of pine as I said. He added math to his argument and I caved.
After that, every door became an exercise in my father pulling out his two ten foot poles prior to even trying the handle. My sister, bored, spent most of the time doodling on her character and having very little interest, and my mother began to make humourous jokes about every odd word that came up. Not good jokes, mind, just derogatory things about who invented the word 'orc' and how did pig-faced people wear a helmet if their eyes were on either sides of their big noses and so on. My father began to join in on these also and things did not go well from there. Frankly, within an hour, they weren't capable of taking anything seriously, from the word 'charisma' to descripe attractiveness to the word 'experience' to describe points needed to 'win.' The combination of words, 'hit' and 'point' seemed to send them into paroxysms of laughter.
I felt totally inadequate. I couldn't express how the game could be good, I couldn't demonstrate it to them, I couldn't get past all the mockery and I definitely didn't have the raw knowledge of the game that I needed to DM these terrible people.
Well, they had the same basic reaction when I said I'd be a writer. And the same basic reaction when I said I'd go into the theatre. Which they acknowledge now that I've done a good job with. Like all parents, they don't remember at all having anything against those things.
But they still don't 'get' D&D. And a repeat attempt to teach them has never been given, and will never be given, so there you are. It is mostly because this is the pursuit I've never made any money at. If I somehow turned it into a living, their selective memories would kick in and they'd accept me playing this game, also.
I suppose I've written this out as a parable of sorts, to remind people that there's a definite limit to how many people will ever play this game. Some are just not going to get it - and when you find yourself facing these people, who have arrived at your table following their girlfriends or their boyfriends, I strongly recommend that you gently explain, that you encourage them to watch and not to play, and that later, much later, you threaten your players with a nasty thonging if they ever dare bring around that person again.