I made this thread a long time ago. Or at least a thread like it. You see, I like to make friends. Most characters in the game can become your friend through quests, or by investing in their stores. However, some people require you to drop random items in hopes that they will notice it and ask you for it. I did this once with Aerin in Riften, but I forget what I dropped and every attempt to drop things on my new character has been met with silence.

Has anybody ever figured out how this mechanic works? Do NPCs have certain items that they tend to ask for, or is it completely random? I want to befriend the world.

I think it's random but mostly only happens when armor is dropped.

They always say that they'll wear it but they never even move to pick it up.

Hroki wanted the Ebony Armor I dropped.

Be warned:
Sometimes dropping items in Riften...

Yeah, they never pick it up, but it instantly sets your relationship to "friend". But only a few characters ever seem to react to it. Half of the time, Mjoll ends up killing Vulwulf Snow-Shod in a bar fight. Seems like it's supposed to be a brawl, and starts out as one, but Vulwulf always pulls out his sword and then Mjoll kills him.

I dropped a Diamond in the Inn there before. The old man in the fine clothes killed the Dunmer in fine clothes.

So we've learned that people in fine clothes will kill each other for fine diamonds. Shocking....

Lol I was in Riverwood once and was buying up iron from Alvor for my homestead.

I saw that he had some iron ingots under his armor upgrading table and was thinking about stealing it.

Just then the town drunk guy comes up to me and says "Weird the stuff that people leave laying around." or something like that then walks away.

I turn to steal the iron ingots and they're gone.

The dood just stole Alvor's iron ingots and got away with it.