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So after hundreds of hours of playing this game I thought I had seen everything, then when I was exiting Warmaiden a young mage approached me and asked if I could teach him about wards. I have zero DLC or mods and I was quite shocked. So we stepped outside and I let him cast a few spells at my ward and he thanked me. Has this happened to anyone else?
Also, one time an orc in imperial armor approached me and said he was collecting taxes. I refused and like 4 bandits jumped out of a bush and attacked me, this has only happened once ever. Have obviously been attacked by thalmor execution squads and assassins, hired thugs.
Also, I've had nearly naked people run up to me saying they escaped some dungeon and asked me to go there and kill them. I've also had an old orc ask me to give him a good death.
It astounds me after hundreds of hours I still get new random encounters.

I have a suspicion that the % probability of various random encounters might be determined at the beginning of a new game, when a new character is created. For example, I've had some characters that met roadside Skooma dealers at nearly every bend in the road, while other characters met maybe 3 or 4 in several hundred hours of gameplay. Certain aspects of this game just seem to be weighted differently on different play-throughs.

Oh, that's just the Radiant AI at work. Every little statistic effects everything. Ever since I stopped having characters with beards, I've been met by would-be assassins and thieves constantly.

yeah I've met drug dealers, I've met looters that were looting the aftermath of a skirmish between stormcloaks and imperials, and I've encountered most non magically inclined races, in which they proceeded to call me a milk drinker and a dialogue option for fighting to the death came up

Oh strange random encounter, I've been walking down a main road and there's like 3 bandit chiefs just walking in a row, get too close and they come after you. Have randomly encountered a group of storm cloaks that skirmished with a group of imperials, and I've been robbed by thieves and highwaymen.

I think that mage student approached me because I'm adept in restoration, and if you're robbed as a member of the thieves guild you can get out of it.

Oh also, jfc, I've encountered the companions fighting all over skyrim. Are there any other rare or random encounters I haven't discovered, I mean after 200+ hours I just had that mage student approach me once.

The Skyrim: World Interactions page has a lot info on the known encounters.

apparently have seen virtually all of them, such a shame

There's still two or three listed online I haven't personally seen. With my main character alone I have way over 1000 hours in this game. Maybe it's my playstyle. I fast travel a lot and many of these encounters take place outside of towns. Also, I'm one of "those" players. I rarely use roads. I take my horse up mountains and travel in a straight line. So I miss the "road type" encounters frequently. I've seen some of the newer Dragonborn ones multiple times, though. I guess the island is smaller or something so they spawn more frequently and closer together. I've seen that ice and fire mage duel like three times.

I JUST TODAY got the encounter where the nobles trying to go to Vivi's wedding are heading home... I ROFLMFAO. It was hilarious.

Some encounters I get all the time, others I rarely see. I've played different characters and put a lot of hours into the game but the encounters I get are pretty similar. I run into Talsgar the Wanderer so much I'm starting to think he's following me! Yet I've never seen him sitting down, as is one of his options. Only recently did I run across the young mage with the staff of resurrection. I've never seen him in any other playthrough.

Seeing the Companions out fighting is pretty cool. Although I did have that random encounter with the wandering bandit chiefs; I think I was level 1. It didn't end well.

Wow, in looking through that list, I haven't seen a good deal of those because my characters are usually not out at night. I'm missing all the adventure!

Just today, I ran into the Headless Horseman for the first time. Such a cool encounter.

...Hm. I think today was the first time I ever traveled on horseback at nighttime. Wonder if that's related at all?

Cessair wrote: Also, I've had nearly naked people run up to me saying they escaped some dungeon and asked me to go there and kill them. .

I first saw this only on my 4th playthrough, after God knows how many hours playing the game... really cool that no matter how much you have played, there always seems to be something new!