Day 2: First person you introduced to D&D. Which edition? Their first character.Mike Javernick. He was my next door neighbor. We had grown up playing Godzilla and Rhodan together for years. Coloring huge murals, playing army, all the stuff that kids did back in the 70's. We did it together.
But we had grown a bit apart once I got into Jr. High. Now that I was in 7th grade and Mike was in 6th, not only did the year separate us, but so did geography. He went one way every morning while I went the other.
Dungeons and Dragons though brought us back together. I got the Blue Box for Christmas in 77 or something... And immediately went over to Mike's house. I had played AD&D with my buddy in Jr. High, but I was about to introduce Mike to the glories of dungeons, skeletons and gold myself! So the answer to the second part of that question is: Holmes Version of Dungeons and Dragons.
I can't really remember the character that Mike started up, but I THINK it was a magic user. We didn't really understand the way that spells worked, so we allowed his character access to all of them. Heh. I do remember when his character first died though. Oh my... what a fit he threw. Yeah, we were pretty into it.
Day 3: First dungeon you explored as a player-character or ran as a DM.
And then of course, since that was the only module that I owned, I ran it for Mike, his two younger brothers, his sister and my sister (who were best friends as well). What fun! We loved it. Well, I certainly did. And Mike still talks about playing Dungeons and Dragons to this day. I don't think that he ever played it afterwards, but we certainly played as much as we could. Every opportunity we got, we sat down and played.
Day 4: First dragon your character ever slew. (or some other powerful monster)Huh...This is much harder. I don't really remember, but I'll take a shot. The first powerful "Cool" monster that I remember slaying was a Bulette. It was much later in my character's evolution and we were being ushered into the G series. If I remember correctly, our characters were traveling by horseback across the plains just south of the Vesve Forest in Greyhawk.
The beast naturally ambushed us and took us by surprise. After just one round we were a few horses shy and in dire straights. We won out, but afterwards my buddy Fish told me that it was just a bit of a test to see how we'd fare against something tougher, before we took on a whole slew of giants. Although at the time I had no idea what we were headed into.
As far as dragons went, I honestly have no recollection of battling a dragon before the G series. But those days were long ago and I certainly don't remember everything all that clearly.
Day 5: First character to go from first level to the highest level possible in the given edition.The character that I was speaking of above was one of two that I ran from 7th grade all the way into University. The system was AD&D and the two characters I ran were a ranger named Sparrow Hawk and a thief named Fire Fox. Yeah, a bit goofy I know. But I loved those characters and they're probably my favorite to this day.
I was a huge fan of Wizard of Earthsea and Fahfrd and the Grey Mouser. So they were patterned after them. Granted, Sparrow Hawk had a bit of Aragorn in him as well of course. JRR's work was my foray into fantasy after all.
They started at first level and by the time I was in University they had climbed all the way up to 18th. They were the highest characters I had ever played in AD&D. Now of course other versions of the game seemed to accommodate higher levels. But not better. That's a story for another day though.