Freshman year in high school, about 15 years ago.
Now, my parents and my dad's brothers picked up 1E as son as it came out. They had some of the basic DnD before that. I was born in '74. So from pretty much the day I was born, I went to sleep once a week to the sounds of my dad, the DM giving my uncles hell. (Ask me some day about the chest with the cat statue on it, or the ever increasing teleport.) So it was natural that I would take an interest. I think I learned to read on those books...
So by the time I got to high school I had read and re-read those 1E books. I had been attending a christian school, so playing was out of the question before then. Anyway, one day at lunch a friend of mine mentions he likes to play DnD, and I told him I'd like to as well. So next week, he brings his books.
I chose an Elven Thief (which would set the tone for the next several years). We were captured and put in an arena to fight for our lives. Just the four of us. The arena doors opened on the other end, and a dozen goblins came pouring out, plus a hill giant. The other characters squared up for a fight. My character ran for the hills. I kept trying to climb the arena walls to get away. The audience kept pushing me back in. So I eventually turned, knocked an arrow, and rolled a critical hit. (This on the very first attack roll I ever made.) Speared the giant in the eye, which fell and crushed several of the goblins. Only my character and the wizard survived the fight, the fighters were dead. We got commendations for our fighting prowess and bravery and offered a job. Unfortunately, this was during lunch at the high school. The principal came by and told us we couldn't play that here. that group never did get anything going, but I was inspired enough to start inviting my friends over to use my dad's books to play after that.
Then I started playing any game I could get...