Well in a way my main characters' whole playthrough has been one big YOLO moment because when I made her, it was my first time playing Skyrim and I had no idea how the difficulty worked, so from level 1 on up to like, 40 or so when I learned better, I played her on Adept difficulty. Now that may not sound like much, but to put it in perspective: I was a Skyrim noob, playing a squishy mage with no racial benefits - my main is a Bosmer, not a Dunmer, High Elf or Breton, the so called "mage races"; though I gotta say Command Animal (the Bosmer racial ability fyi) saved my butt more than once. Did you know Command Animal works on trolls, but for a shorter amount of time than normal? I found that out the hard way lol.
I also didn't learn about magicka regen enchantments or Flesh spells until over level 20, so there was that. lmfao I was such a noob back then!
But besides all that, I can think of one event in particular where on the same above character I had a YOLO moment. I was re-playing through the Dawnguard DLC (had to due to a glitch), and I was going through the part of the Forgotten Vale where the Word Wall is and the twin dragons pop up out of the ice. Now I defeated them fairly easily on my last playthrough, so I wasn't expecting a huge challenge. Only I've gained quite a few levels since then - my character is level 63, almost 64 right now, and as we all know enemies scale to your level - and I've also upped my difficulty to Expert because of my character being a higher level and beating things a little to easy on Adept prior to this. Funnily enough I was just considering upping it to Master right before this. Good thing I didn't.
So anyway these twin dragons were hella hard for me to defeat this time. I died twice before I finally succeeded. It didn't help of course that Serana was in bleed out mode 5 minutes into the fight, and that my characters conjurations kept either timing out - and I was out of potions to extend the time by then - or got killed damn near instantly by dragon fire. What finally changed things around was me thinking to take advantage of the landscape. In desperation I healed Serana and summoned a Boneman Archer to take the twin dragons attention off me long enough to find some sort of shelter I could kite them from. Of course the only thing nearby was the wayshrine up on that stone hill, but it worked. The poor Prelate cowered the whole time, I felt so bad lol.
But this way I was able to hit it with some Dwarven Crossbow bolts and dodge back in. This combined with a few more summons and some poisons brought down the first dragon - at which point I made a save so I wouldn't have to do it all over again, a bit of a cheat I know but this was hard enough to accomplish IMO that it was warranted - and by then Serana had recovered and with her and my summons help, I was able to finish off the second. I'm not kidding you when I say it took me an hour to do this. I checked the time. I don't know how people play on Legendary and think that kinda thing is easy man. Seriously. Maybe it's because I don't really cheat - I don't use things like the resto loop or the trick to level your skills to 100 in one sitting or anything like that. I'm not saying anyone that plays on higher difficulties do, just explaining why maybe it's harder for me. I mean I don't even like using potions in mid-battle or Dragonrend on dragons, or saving in the middle of really hard battles so I don't have to do it all over. If I don't feel I have to I won't do that. Anyway so that was my YOLO moment. I could've easily left Serana behind and snuck off somewhere or even used the wayshrine to get out of combat and teleport away from the Vale. But after dying twice from those bastards I wasn't going to leave until I killed them both. And so I did.
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