I almost exclusively do all drugs alone, especially tripping. Much like you when I was younger I never thought I would literally prefer to be alone while tripping and rolling but thats how I like it. Rolling is a bit more malleable as I basically roll alone half the time but normally try to find things to do.
My normal trip, usually on LSD, consists of me taking 3-4 hits at about 10am and going about the day. I can either go downtown, to the park in my city, or walk the streets. I like it because it lasts all day so I can do a multitude of things, other then trip at night and sleep. I usually go for long walks or do something crazy like bring a bunch of nitrous and stumble about the park covertly inhaling from my backpack (did this in the streets of nyc and the subway, pretty proficient at loading the things quickly and i am to assume stealthy) but i wouldnt do that if i had someone with me. One person can easily go unnoticed, I also dress nicely and in a sense run though everything one would do for a date, cut my nails, shower, shave and trim my beard, put on decent clothes either nice casual or leaning more toward "dressy in appearance" never some tie dye or miss managed clothes. The idea is if im in nice new clothes looking all done up no one will assume im on or doing drugs. If someone sees me inhale from my back pack but i look like i have a good job/life they are more likely to assume something other then drug use, people judge by appearance first.
It also helps that acid is not debilitating and i hardly get visuals (not that i want them) for me its all a mental game. LSD makes me have clear focus, good foresight, and mental stimulation (i say its like being able to think of 3 things to say instantly rifling through them and picking the best one in under a second) ive handled cops, coworkers, my parents anyone on LSD they cant tell because if anything i am "more witty" then usual. I absolutely love lsd for that reason its like me^10 all my greatness enhanced coupled with energy and confidence. This is why i cant trip with people i have a bunch of what i call "self imposed tripping regulations" so when in i want to go downtown i look like im doing it for a date haha.
I could trip with a few people, my younger brother being one of them. He's a lot like me in the mental aspect, doesnt lose his sharpness but he gets a bit more funny. My roommate becomes a complete retard and dresses like a hippy so i avoid that whenever possible. I dont mind if he enjoys it but your only as strong as your weakest link and if he cant compose himself around police, which he struggles with sober, then he cant trip with me.
I am also not to social so it makes sense that i wouldnt want to "waste" my trip being around people.
