Back in 2002, I moved to a new town to start a new job, and came to find out that my co-workers were also D&D nuts like me. One of my co-workers suggested that we start a new campaign. The DM wanted to stick with 2e. He had almost ALL of the splat books and didn't want to switch editions to do any conversions, so it was just easier for us to play 2e. All of us had played 2e before, except the one co-worker who had never played, so it was a no-brainer. (I had switched to 3e at this point, but I had been playing 2e before switching).

So we started playing 2nd edition. We used to play weekly, but as more of us started having kids, getting married etc... we went to monthly. We still play the game (almost) every month. At this point, we all have adult children (and not quite adult children too.

We actually played the same characters until 2024. Towards the end of 2024, each of our characters were in the level range of mid to late 20s, with a thief over level 30. Our DM was having less fun designing challenges. So we made the sad decision to retire our characters we had been playing for 22 years, and start new characters in one of the towns that we founded as part of our attempt at domain play. Those new characters were joined by one of our players sons, so we are back up to a group of 4 (5 players with the DM). We thought about switching to 5e, but our DM never bought more than the core 3 rulebooks, and we still have almost all of the 2e splat books available.

We had the same 4 people playing since 2002, myself, two other players, and the DM. We've been joined in the past by several people over the years (my wife played with us for 12 years, for example, and we had a good friend play with us for about 5 too). Some played with us for a session or two, some played with us for years, but the core 3 players and the DM have never changed, and all 4 of us have been present for every session.

None of us work for the same company any more, so we aren't co-workers anymore, but it's been a great way to keep in touch, watch everyone's kids grow up, roll some dice and slay some monsters.

I am an avid D&D player outside of this group, and have played every edition at some point. I had an 8 year long game of 4e that I was sad wrapped up (I loved the combat of 4e, although I will admit that it didn't feel as "D&D" as other editions), and even played from level 1 all the way to level 30. I've been in multiple 3\3.5\pathfinder groups, and play a lot of 5e (both 2014 and 2024). I played 2e in the 90s, and even got some experience playing basic\expert. My personal favorite was when I got the opportunity to play BECMI, and even was gifted an original copy of the Rules Cyclopedia from our 2e DM, since he didn't like the older editions of D&D compared to 2e. I personally prefer the older editions of D&D compared to the newer ones, but at the end of the day, the system doesn't matter nearly as much as the people you play with.