Trigger warning

All that I had to hold onto was that I would climb out one day. And then I was gonna torture you. Nice and slow, like pulling the wings off an insect. But whatever I do to you it's nothing compared to what you do to yourself, is it? I can see it in your eyes, Dean. You're worthless. You couldn't save your dad. And deep down you know that you can't save your brother. They'd have been better off without you.

Read more: https://www.springfieldspringfield.co.uk/view_episode_scripts.php?tv-show=supernatural&episode=s02e14

Did you read that? Ok I hope you did because that's what inspired this sad headcanon.

In season two Meg says what's up top. What got me worried tho was when she said "But whatever I do to you it's nothing compared to what you do to yourself, is it? I can see it in your eyes, Dean."

So the headcanon is that Dean self harms. Maybe in a different way then cutting. Maybe in a way that Sammy or Bobby or anyone else wouldn't notice without looking specifically for it.

Whatever he does to himself, it's worse then what Meg could do if she tortured him.