I once did a terrible number on this poor girl by sharing 3 doses of shroom tea with her - because the third person didnt show up.
At the time all i thought was "all the more fun for us" - but she was anxious, terrified. It was horrible.
I had an incredible trip, in terms of visuals and synaesthesia - but i also had to baby-sit her, and feel like the reckless idiot that i am for inflicting such shit on her mind.
I was a bit naive of anxiety in those days (mid 20s). Learned a lot (generally) since then.
What i do remember most clearly about that trip though - not especially "difficult" a trip as far as im concerned....but i had this period of being struck by this enormous cavern of ambiguity that i became aware of having deep in my psyche.
Like you and i say above - there are no answers, there is no certainty. I just realised that even my strongest beliefs were (at least in part) an illusion.
This struck me as deeply, deeply sad - and i had this big full-bodied sobbing cry (no dount bought on by my trip buddy's troubles) - which actually felt amazing. Healing.
A bit like how the manic laughter of LSD can start getting confusing - even annoying - these tears felt...maybe not "good" - but such a release.
Whatever you choose, man - i dont need to tell you (!) - set and setting.
As a good, wise old-school head friend of mine likes to say (about anything vaguely or specifically related to psychedelics);
"It's all part of the trip"
Wise words, i think.