Hmm. I am pretty sure my first server was Shadowmoon as a NE Rogue. Then Elune, Firetree, etc. – i did a lot of fresh server starts because I enjoyed the thrill and excitement of new server feels/progression/communities.
F R E S H
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Stormrage - Horde, from Vanilla to Wrath of the Lich King. Anyone from the old guild Utopia?
Argent Dawn -> Dalvengyr when it opened
Dethecus, from day 1 until Cataclysm.
Shout out to my old guild Storm Forged!
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Wildhammer
Nathrezim …
Gorgonnash was my vanilla realm. Stayed there until the final Legion patch, at which point it was so dead my guild made the decision to mass transfer off because there wasn’t anyone to recruit or anything. I hated abandoning our home and was one of the last couple hold-outs to resist the transfer. Each of us transferring to our new home ran about two-thousand dollars total. >.>;
It still turns my stomach that Blizzard has made so much money from letting realms die. We were one of the last really big guilds to bail from the server and I really wished we could have stayed and tried to salvage the community but it had been steadily declining since MoP and was beyond repair.
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Alleria, Alliance.
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Alleria was my first realm also, I remember a few guilds from back then… Risen, Azergarde, Silent Reign… I was in a casual guild called The Fellowship. Good times.
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I was also Balnazzar (Horde, Mute Assassins and Nerd Fury)…what guild were you with?
Also Horde 
We were Methods of Supremacy for Vanilla. A few of the leaders got poached by Sacrifice during Kara progression and so we remainders formed Alt F Four.
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The guild sounds familiar but i was in a guild called Raging Sun. we raided up to Naxx.
Detheroc woohoo!
Played on Laughing Skull as an Alliance Priest to 60 - got into a guild that could not progress through MC and then started fresh as Horde on Detheroc with a bunch of RL friends as a Druid (Nahyo). Detheroc has been my home since ![:slight_smile:](https://d38bqls1q93fod.cloudfront.net/en/wow/images/emoji/twitter/slight_smile.png?v=6" ":slight_smile:")
My first character was on Windrunner, Alliance side, actually on this exact character.
Made him December, 2004 and he’s been my main ever since! Jumped between a bunch of progression raiding guilds in Vanilla and didn’t find my current guild until BC.
Hyjal - Day One - Undead Warlock
Stormscale - US.
Was a Tauren Hunter named Akiak, Only guilds i remember i was in were Cohesion and Seven Sins
Bloodscalp - Desk Chair Lamp - Mathuzade
I remember the endless PvP between Tarren Mill and Southshore with the Heavy Hitters guild.
Kargath 4 Life
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Kil’jaden and Smolderthorn Then Trollbane in BC
I can’t remember the very, very first server I ever played but the second time I played was on Ghostlands because the friend I was gonna try the game with went by the username GhostXero or something like it. We only played once though and it was just him showing me around the Darkmoon Faire.
Wonder where he is now.