Red Faction demo in late 2002. Just grabbed it wanting to check out what online gaming was about. In 2003, I got the full game for my birthday. That lasted until 2005, when I found the disc with a crack in it thanks to my brother.

Fortunately I bought it on Steam just so I could play it again, and even then people were still playing. I did get the Red Faction 1 + 2 bundle here when it was released and on sale. I bought Red Faction again (which is DRM free, thanks GOG) as well as get its sequel too (has no online play, but I enjoy it nonetheless).

Would anyone believe my 1st and only multiplayer experience was Windows Checkers. :D

Well, I tried a D2 game once but I didn't know anyone and I felt like an asshole just showing up in the middle of someone elses game so I logged off.

Oh I remember that one, it was basically like a couple of rooms you could fool around in right?
I started that one up to check the destructo engine with a friend of mine and after a minute or so some random stranger connected.

Marathon!

On LocalTalk I believe. Got really into it, made some levels, some of them even got ported to Quake by other players.

Was incredibly pissed when Bungie sold out... still hold a grudge ;) I'd love to play the Halo series but never had the right hardware!

Yup, I use to play private games with my friend. I think the map you're referring to is called Office Space. I once destroyed a hole in the corner of a room and used a sniper in it.

Was password protected so all we did was play and fooled around with geo-mod.

My first was with Day of Defeat. My dad played it a lot when I was young and he would occasionally let me play. I wasn't very good, but I still remember my first kill. I can't remember the name of the map, but I remember what it looked like, and I remember that I did it with a grease gun.

Aside from that, however, I never really played online until I got Halo 3. I played that quite a bit, but I never renewed my Gold subscription because I didn't play online enough to justify the cost. Even now that I have a constant Internet connection on my computer, I rarely play online, partly because my connection isn't that great (especially when other people in my house are using the Internet) but also because I'm just not that big on multiplayer. Mass Effect 3's multiplayer is pretty fun, though.

Oh right, it did have multiple rooms. There was also 'Glass House' or something like that.
It was the first game we'd ever played that automatically published the game on a lobby server, never made that mistake again.

Ah Glass house was fun, I remember always wanting to take a rocket launcher and make tunnels!

There is a map called Lobby, but from what I remember last time I played, it was a server browser.

Well the browser is just to browse, so what do you call the server?
It looks you're intentionally trying to misconstrue what I'm saying.
Would it make you happier if I used the term match-making server?

FIFA 99/00 (that period). First time and the last time I've played this kind of game on a PC.

Apologies since I don't mean to misconstrue what you're saying. I'm not sure if it's matchmaking. I attached a screenshot of what's in game to connect and play on servers.

"Server" at least in Red Faction is either a game someone is hosting, or a dedicated server. At least to my knowledge anyway.

Maybe it's another game you're thinking of? I'm not trying to misconstrue what you're saying. Maybe another game has similar elements I'm guessing.

(Black square is blocking a cus word, I don't know the forum's policy on such language).

What the fuck is with that censoring? :P

I think it's a misunderstanding of terms.
Unless the heat has completely fried my brain, there is a central matchmaking server (or cluster) that contains the server list. So it's a server that redirects you to other servers, a common concept in networking.
A player creates a public server, that server contacts the matchmaking server which in turn adds it to its server list.
Another player wants to join a server, so his client contacts the matchmaking server which sends the server list to the client so it can connect to servers which are on the server list on the matchmaking server.

I guess cussing is allowed here. :P Sorry, I didn't know if it was against any forum rules. :P

Ah, now I understand, the Master Server, at least in the settings menu on the launcher window it's called that. Thanks that clears things up actually.

I am fairly sure it was Duke Nukem 3D or something very similar.
I only shortly dabbled into PC games back then and when I was waiting for my mom to end at work she often sent me into gaming cafe just across from her work. I only tried few games there and never really sunk much time into any. Few times I saw there some regular older dudes (they were over 15 for sure:-)) play some shooting game and it looked awesome and like great fun. So one day I had the great idea and asked if I can play with them. It happened only once and I never wanted to repeat it again. It was slaughter. I ahd no idea how to control it or what to do and I ended up dead every several seconds with not being able to accomplish anything myself. I bet they enjoyed themselves a lot but it made me afraid to play FPS for some time and to play them online for even longer. (I am still not keen on doing it as I already tested that I am indeed not too good in them)
I then played Empire Earth with my friend over LAN a lot but that's not really online experience (and hotseat HOMAM with others before), so my longer multiplayer and real online experience was somewhere in 2009 or 10 I think with World of Warcraft where I spent about 2 months.

EDIT: Actually not. I played online checkers before that and we also spent a lot of time playing some old F1 races in our high school computer classes. :-) That was in 2002 I think.