I just remembered that it has now been 50 years since the release of the original Dungeons & Dragons white box set in 1974.
Hard to believe that’s how long I’ve been in the RP game. 30 years before WoW, and almost 20 years here.
To me, it doesn’t seem that long ago I was rolling up my first fighter in D&D; as of today I’ve had so many characters in so many games it’s hard to remember them all.
How about you folks? What/when was the first RPG you got into?
Original AD&D in junior high. 1983-ish
D&D in the 80s was probably the first role playing game that I somewhat played. Think I was maybe 5?
Final Fantasy is really the game that got me into the genre. While it’s not necessarily you creating a character, you do take on a persona per say.
From there it blossomed. Personally I prefer some old school RPG video games such as Lunar, Lufia, Final Fantasy (of course), and Breath of Fire to name a few. Never got into Dragon Warrior, but its a series people say I’d love.
As for switching back to pen and papper / board games, Gloomhaven kind of got me going back. While I play at lot of Catan and Fluxx with my siblings, a nice long play of Gloomhaven is where it hits home with me. It makes me want to get into D&D or Pathfinder, but I live in a place that isn’t necessarily nerd central. Plus it’s a time commitment I just don’t have anymore.
Now if you talk about RP in WoW… oye! That is going to be a big topic. Wish any of the groups I did activities with were still around. The lack of support / enforcement by Blizz is mostly the blame. Hard to do an event when you have randoms ruining it 
Video game wise the first RPG I probably played was Dark Sun: Shattered Lands in the early 90s. I was a kid and had very little idea what anything did, but figured most of it out through trial and error.
I also played a ton of Diablo and I know they’re considered aRPGs, but I never really thought of them as RPGs personally.
Tabletop my first game was Pathfinder around 10 years ago now. I rolled up a rogue that struggled to hit things without Weapon Finesse.
These days I’ve come a long way and I DM for my table, which tries a variety of systems.
I roleplayed in WoW pretty much immediately once I started in earnest in 2010.
(I played for maybe 3-4 months in late TBC on a different account and I didn’t do it then)
But it was always on a very on & off again casual walk-up basis.
The one time I joined a proper Heavy RP Guild, it fell apart after a month or so, and I basically used that as the story to retire the character I’d usually use when I roleplayed. Name changed it after that and everything (and it has more recently been fully deleted).
Haven’t roleplayed in any notable way since then, and that was probably early 2016 or late 2015.
So, 5-6 years tops and I don’t do it anymore, I guess is my answer to the title?
As far as D&D / Tabletop goes, I didn’t touch any of it until after I started playing WoW. I’ve played like 3 sessions of D&D 5e and 3 sessions + a one shot of Pathfinder. Probably late 2016 - early 2017.
D&D was going well, half of us were first timers and were just getting comfortable roleplaying in that context, then the DM had a bad breakup with his girlfriend and literally holed himself up and didn’t speak to anyone for several months. (He’s doing well now!) But naturally that killed the campaign and we never came back to it.
Pathfinder didn’t go as well. l was having fun, but it was really clear a couple of the players only decided to play because they knew other people in the group wanted to. Between that and a couple people repeatedly not showing up on time (not the same 2!), the DM called it off, and I don’t blame him.
The very first RPG-adjacent product I got my hands on were the microgames Melee and Wizard by Steve Jackson, that would eventually become the proto-GURPS game The Fantasy Trip. This would have been … summer of '82, I think? (I ended up liking OGRE and GEV better, though.)
My older brother introduced me to 1st Edition AD&D in the fall of '82.
So, I’ve been fooling around with things like this for just over four decades.
Original D&D!
Ah, the first three booklets and the fun times with friends that lasted soooo many years!
Interestingly enough, I started roleplaying back in Starsiege. And it wasn’t a roleplay game. But the timeline is 35 pages long and spans the Earthsiege, Starsiege and Tribes game. I was also part of the Writers Guild for it. We spent time doing roleplay and writing workshops with Blake Hutchins, the lead writer. Was super fun. 
D&D Red Box
Hero’s Quest.
It was sort of a board game/D&D hybrid, with a single board with the layout of a dungeon on it, which you then had limited customization over by placing tiles and miniatures like doors, traps, and furnishings in addition to the players and monsters.
You had 4 heroes: the wizard, elf, dwarf, and barbarian, and a prewritten campaign to take them through a bunch of different dungeon floorplans and mission objectives. I forget if it had leveling up, but it definitely had treasure carryover where you upgraded your gear and spells as you went.
My family would play it together when I was in elementary and middle school. I’d be the barbarian, my sister was the elf, mom played the dwarf and wizard, and dad was the DM.
These days I’ve been DMing a homebrew 5e campaign set in not!Ancient Greece around the time of the Bronze-Iron Age transistion for the last two years.