Massively

Back in my Everquest days.... I camped the "Priest of Najena" in Unrest for probably 5-8 days total time on and off.... He's a 24 hr spawn, and part of the quest for the Erudite only Necro shoulders "Mantle of Souls" ... Quite the quest for that one but needless to say I finally popped him, cleared all the adds around him and he pwned me.... =p
I was lvl 58 at the time and had to pawn off my Stein of Maggokk to get a local farmer to help me with him... =p

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I sold an awesome green drop in Guild wars as well but that was a when I was still a noob.
In eve I had gotten to the end of an exploration expedition mission (EEM for short heh) and I was supposed to blow up a hidden station owned by the blood raiders and we all know shooting stations can be extremely tiresome and combined with the fact that the station was in lo-sec meant the reward had to be worth the risk. So I spent over an hour shooting this station and managed to blow it up without any interference but that wasn't the end, I got a BLOOD MESSIAH spawn which definitely means epic loot but as soon as I kill the guy... downtime shuts my client and when I log back in, it was all gone.... I still feel the pain inside everytime I think about it.

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As a lowbie in FFXI, I ran from Bastok to Windurst one day. While leaving Gustaberg, I saw a mob named the Leaping Lizard, but let it go because I was in a hurry. In Windurst, I messed around a little bit in the surrounding area and left another named mob (can't remember the exact name) go. A little later I told a friend about the two mobs I had seen. He informed me that they dropped the Leaping Boots and the Monster Signa, two of the more valuable and rare drops in the game. Needless to say, I could have made 700,000 gil that day.

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My biggest was in DAoC - a staff that had a clickable proc for my Theurgist. I spent months getting it! The day I finished the quest I was so excited my guild thought I was insane. The day after my glorious feat, they changed the clicky proc to be basically worthless.

At least the staff was shiny, but I think I didn't log in for a week in frustration!

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Back in the old days of WoW, my warrior ran UBRS at least 10 times a week for about eight months with NO Valor chestpiece dropping for him. Not even to lose the roll on.

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In my early days playing LotRO I got my first character to level 35 and hurried over to do the necessary quests before I could buy my mount. The actual purchase was over 4 gold -- not a cheap expenditure for your typical character at that level. Unfortunately, I mistakenly bought a pony instead of a horse, and it turned out that my human couldn't ride it. At that time there was nobody to trade one mount for another, nor was any player in need of a pony. So my only option was to sell the pony to a merchant for 1 gold.

A few days later I had the money I needed again and returned to buy a horse. There were going to be no errors this time! I made absolutely certain that I was buying what I could use. Happy to have my mount, I rode down to Bree. While in town I did some crafting and a few other things, then realized my bags could stand to be emptied before I left for more adventuring. I stopped at a merchant and since everything valuable had been put in the bank or up for auction I used the "Sell All" feature. You guessed it -- no more mount. Adding insult to injury was the fact that I had sold too many items for them all to appear in the buyback window, and my horse was gone forever.

The next time I bought the horse I made sure to go to a merchant immediately and lock it so that it couldn't accidentally be sold again. But that first mount cost me almost 12 gold by the time I was done!

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I know I've done things like this...but I can't think of any at the moment :(

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Back in the days of WoW when Onyxia was end game, my mage saw the netherwind crown drop twice. The first drop, it went to someone who was higher up in the guild than I, and thats fine. The second time the crown dropped? It went to "a friend of the guild" who had just come back to start playing his mage again. So he gets this helm that by all rights shouldve gone to the dedicated guild member, and what does he do with his ill gotten gains? quit playing a week later, never to raid again.
I ran ony countless times trying to get that helm to even drop. No dice. I stopped running her after my guild devolved into asshattery and we went our separate ways.
Finally with this newest patch I got that helm that has cursed me for so long, and I wear it proudly.

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In Diablo 2, which was as close to mmo as I got at the time, I was slaughtering mobs in the cow level with my 80something bow amazon. The horde was dieing slowly and at the back a mob went down and dropped a unique Colossus Blade (The Grandfather). Before I could finish off the cows between me and it, a sorc teleported in, picked it up, yelled 'I found GF!!!' in chat and left the game. I never got it back.

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While playing WAR, Destruction on Phoenix Throne had just invaded Altdorf. I was having fun running around, killing Order, trying to figure out just what the hell you are supposed to do there. About that time my IRL friend started bitching to me over Skype how we weren't playing together, and to throw him a bone I decided to leave the scenario and help him farm the 1000 Living Armors we needed for a tome tactic unlock. Farming those guys was a lot of fun and I ended up getting some really nice weapons and even dyes out of the deal.

On my way back to IC, the game had my character reload from the most recent save spot: coming out of Altdorf. I lost all those kills, all those items and all that gold I had collected over the last 2 hours in that moment. That was the beginning of the end for me and WAR.

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just for fun

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You got served! doesn't mean you got beat or owned.

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Two words: Assault Jerkin.

OOOOOOOOOOOOOOOOSSSEEEEEEEEEEEEEEEEEE!!!

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