Started playing D&D when I received the black box for Christmas sometime between 1990 and 1993. I ran a Campaign out of the box for my dad and my sister for a few months, and then for a bunch of friends for a year or so. In 1994 I discovered AD&D 2e and ran a campaign every Friday night until I graduated High School in 1997. I continued to keep up to date on D&D over the next couple years with my subscription to Dragon Magazine.
After flaming out academically at College, I moved back home where I ran an irregular game for my sister and some of her friends who were still in high school while I was working at a small book store. When D&D 3e came out, I used my book store discount as an excuse to be a day one adopter of the new system. I bought the PHB and was running a campaign with the new rules before the other 2 books had even hit the shelves.
Unfortunately, that short campaign was my only experience with 3e. Before the Monster Manual had been released, I had relocated 250 miles north, and the only people willing to play with me there were AD&D 2 hard cores. I played only 4 or 5 times over the next few years before relocating again, this time 600 miles east.
The next time D&D came into my life was the era of D&D 3.5. I was again working at a book store, so the changeover from my 3e books to 3.5 was seamless. I played a weekly game in my garage for about a year before I was transferred once again, this time about 150 miles from where I had started, but into a community where I knew no one to play with.
Years passed, Dragon Magazine ceased publication, cutting my last reliable tie to the gaming community, I drifted away from the hobby, 4e only a dim flicker on my radar when it was released. I believed I had played my last D&D, I had even sold a bunch of my older editions, and my more valuable miniatures. Then my sister's boyfriend asked me if I would run a game, a one shot, while I was in town for my sister in-law's graduation. I said I was rusty, but if he really wanted to learn to play, what the hell. I used an old game day (2010 I think) scenario, running it for him, my sister, my brother, his boyfriend, and a friend of my sister's boyfriend, and had a blast! I came home determined to find a way to keep playing.
That was when I stumbled on roll20.net. It is the perfect set up, and I easily set up my first session, and have been hooked since.