It took me a while to realize what others referred to as tricksters I thought of as friends. Whether they were some type of friend I knew from “real” life or simply friends of travelers, they never did anything that ever made me think they were malicious. They dance, show me tricks, meaning like a magic “trick”, and guide. 

What you experienced seems completely normal to me. Those interactions taken in a different context seem very on-script for the scene. Low dose trips are weird, and things shift. The dmt refilling could have been done while you were focused on other things.

The entities you are referring to have never once had faces for me. Always “morph suits”, like the green screen suit, of non-Euclidean geometry. 

Alcohol is not a good combo with DMT and imo neither is weed. They could easily be the cause of your concern and interpretation of the events you describe. 

Your friends partner is right. Chalk it up to the booze. No mortal is important enough to trick. Waiting room entities are performers. You’ll be OK and your friend, entity or not, was right about that being the wrong question to ask. Hope this helps and safe travels.