"I tried to go home. That was stupid. The servants screamed at the sight of me and ran to fetch a priest. I ran, too. Into the only place where I was safe, into the dark. And that is where I've stayed ever since. It's where I belong Elena..."

There has been something that has stumped me ever since I first read The Vampire Diaries 8 years ago. What on EARTH was Stefan doing for the five centuries between his mortal life and his arrival in Fell's Church? I've thought and thought about it, but I really can't come up with anything. The only details left to us are that after being threatened at one point by Damon's return to Florence, he found sanctuary in the woods and "remained in the darkness as he belonged." Now that's not telling us a whole hell of a lot.

With his brother Damon, we know he was a mercenary for some time and even after that... well it takes little imagination to figure out how Damon could pass the centuries. Women, hunting and keeping tabs on Stefan. (LOL the exact same thing he does in the 20th century, imagine that!). And Katherine spent centuries learning the joys of vampirism from Klaus and then plotting her revenge. Klaus was crazy, therefore had a constant source of pleasure and amusement.

But what was Stefan doing? Sure he was mourning over the loss of his love, but we are told in The Awakening that he hadn't allowed himself to think about the actual events surrounding Katherine's "suicide." So he wasn't replaying the tragedy in his mind over and over again. I just can't imagine anyone sitting in the dark of the forest for 500 years, doing nothing but feeding, sleeping and moping. You can't come out of such a life sane enough to reenter society. And I'm fairly sure he couldn't have had a relationship (platonic or otherwise) with anyone, or else befriending Matt and Elena wouldn't have been such a shock and trial for him...

Another thing that puzzles me is his money: he obviously has a lot of it. He dresses expensively and drives a Porsche, but his money couldn't have come from his family. To have died and come back with nothing with the clothes you're left with means to start over monetarily, and somehow he seems to come out pretty wealthy by the 20th century. So obviously he had to have SOME role in society, right?

So I'm just at a loss. Stefan's one big enigma, he is. ^^ Any theorists or fan fic authors who want to contact me on the issue, please do!