Hello Out.of.theashes, much of what you write resonates with me, particularly about not quite being connected to people and having difficulty staying at the chit-chat level of conversation. When I do connect I tend to communicate in "flashes", speaking very rapidly and covering alot of ground with whomever I'm talking with.
So far most of my DMT experiences have not been "spiritual", though a couple definitley were and involved my wrestling with inner demons (anger). I'm hoping in time to learn how to better use this tool since the short duration of vaporized DMT means I have more opportunities to explore with it compared to other tools.
As you consider entheogenic exploration, your intent is extremely important and will have alot of effect on the experience. Answer for yourself what and why you want to explore, work on, see, think about, whatever. You don't need answers, only questions which can form a loose structure for an experience. I've found that asking myself these types of questions and writing them down before tripping makes for a more meaningful experience, even when no answers become apparent during the trip. I really wish I'd known this in my early days of chemical based exploration.
Many have suggested starting with shrooms first, and that sounds like good advice to me as well, though I haven't had the pleasure of my psilly friends for over a decade. Sigh... What I have discovered as a very useful consciousness exploring tool is mescaline bearing cacti. If ever there was a material that almost always results in therapy it is mescaline, at least for me anyway. Connectedness? Mescaline helps to remind me that I am connected with everything and everyone; I can see it, feel it, be it, and know it long after the trip has ended. The only downside of cacti is the time it takes to prepare the material for ingestion and the duration of the experience, 16 to 20 hours being my norm. I have few opportunities to book such a large amount of time for this, but when I do I always get something out of it. If I was to recommend a first time entheogen it would be cacti.
Thank you for prompting my thoughts! Good explorations to you!
CS
A scale is a wonderful thing. Everything else posted by CS is lunatic fiction.