I've had a few rather amusing bumbles over the years.. I guess I'll share a few with the class for entertainment purposes.
This was likely my first attempt at actually playing the game, rather than just constantly remaking level one characters trying to figure out the "optimum" starting setup. I'd made an Elven female Mage/Thief hybrid (low level enemies, cower before the might of high dex + harm), sporting an elegant dress, lockpicks, some ladies boots that I'd found in a trash can in Stillwater, soft delicate knuckles that I'd figured were unfit for the painful experience of wearing gauntlets and a small selection of spells.
After my trek to Tarant and finding a quest to go retrieve an elven artifact, I thought it a good idea to go complete the quest, at the very least for additional funds. "What's this!?" I said, as I saw a section of town that I'd completely skipped while entering the city. "Slums?", I thought. Well, after tactfully mousing over the rough looking half-orcs just inside and seeing that they had an "amiable" reaction towards me, I figured, "I'm part of the Underground. These people will accept me with open arms!". Forget the guards warnings about this "Boil" or whatever, I'm going in! ....And was subsequently butchered in about three seconds flat. I hadn't saved once.
This play through, I'd had access to a map of the whole continent, so I knew the location of Qintara, along with the location of the pass to gain access to Qintara. Yet again, I was a magic using Elf. I was figuring that the "best" magic equipment would be in Qintara, and beings as I'd already amassed a small fortune thanks to the purchase and exploitation of two manuals (herbology and explosives), just buying cheap ingredients and then selling the salves/grenades back to shopkeepers for insane profits (and stealing from shopkeeper chests - such as the inventor), I figured it would be a lovely time to get some quality magic arms and armor. So, I ran to where the pass was, manually, as I couldn't place a worldmap marker at the exact location of where the pass would be. Found the pass, and instantly exploited Teleport to get to the other side without having to fight (it works/worked), and off I went to Qintara.
Though I was disappointed with the lack of significant upgrades to my magical equipment, I was pleased with finding the place, and thought nothing of any significant side effects of entering the Elven city to soon. Later on, however, I was trapped (or so I thought) in Stillwater/Qintara, as Raven would never show up, because the Elf in Stillwater wouldn't give me the location of Qintara because I already had it. Not knowing that I could just take his amulet back to Shrouded Hills and bypass this, I fumbled blindly for at least another twelve hours of gameplay before I gave up and just put the game down for a few months.
This time, I was actually using a tech character, though I can't exactly remember the race I used. Likely a human, because I've never really been keen on Dwarves in any game.
I discovered the truly awesome power of the throwing skill, and, more specifically, the pure destructive power of grenades (explosive grenades, specifically). So, after about an in game "month" of making six explosive grenades per day in Tarant, buying the materials from the general shop, inventor, and gunsmith, I figured I was good to go. I had a significant stock of grenades on myself, though not enough to slow me down to much. I was "smart" and had Virgil serving as a packmule for my extra stock.
Now, I don't know if anyone else has noticed this, but Virgil never learns any skill in throwing. And to say that "Virgil throws like a girl" would be critically inappropriate. Virgil does throw quite well, actually. And often. And he also, apparently, discovered the RAW destructive power of explosive grenades. However, he apparently never noticed that he was critically failing at throws like crazy, and ended up blowing my character up instead of the enemy.
While it was comedic initially, my amusement quickly turned to anger when I realized that, yet again, I hadn't saved once during my entire time hoarding grenades. So, even though I was at around level twenty or so, I still ended up getting self-decimated by a random group of three ailing wolves, thanks to Virgil's impeccable throwing arm.