Nobody's ever produced a movie that comes close. Plus, it's not something you just watch- you are totally immersed in it.

You seem like you have a bit of work to do. I can't say how DMT would affect you if you were to try it in your current mindset. You may actually have a hard time processing your experience, it will be so far out.

If you have access to shrooms or acid, you may want to try a small dose of one of those first. This gives you some time in the psychedelic space, a chance to familiarize yourself with the experience. These substances bring on an experience that's essentially in the same basic spectrum as DMT.

If weed alone is enough to set you off on a dark trip, a psychedelic experience could have the potential to be pretty rough. On the other hand, it might show you something you need to see.

Think twice about having a sitter who is too much of a character liability. The experience could end up being all about them, which could be a real drag.

I hate to say this, dude, but you need to break this cycle and start making friends. Trust me, I know where you're coming from, being the awkward quiet type. I used to feel paralyzed in social situations. But the more I learned to just relax and be myself, the smoother I found I could relate to others. And yeah, you're taking small risks by letting people into your life; but avoid it too much and you're missing out on a key component of being a social animal.

A little psychedelic reset would possibly do you some good. However you get there. I HIGHLY recommend that you read extensively throughout these forums.

You seem to be looking in the right direction... Keep seeking. Your answer is out there. Trust the process, you'll find what you're looking for.