Update: My friend makes electronic music so we agreed he should try and "play" some original music in his mind for the entity, being the jester is a performer who could probably appreciate music.
So last night he noticed all the usual signs of this dream starting. And he was lucid enough this time too follow through. As he approaches the entity he starts humming a tune in his head and the entity's expression becomes unambiguously happy. Apparently the jester started "bobbing along" and thanked him as usually it is him who has to do the entertaining and he enjoyed being entertained. The entity was then "throwing" other jester like entities at him while singing something along the lines off "The jesters want to say hooray to yoooooou, they want to come and say good day to yoooou" The "dream" finished with a feminine entity that was thrown at him, embracing him, clutching his face with both hands and asked him to pass a message on too me, along the lines off "Say hi to Daniel for me, we're looking forward to seeing him again."
Not to insert my own agenda/opinion into it, but it's interesting because i have only had 1 dmt trip, where i was met by a feminine entity who ended my trip by clutching my face and blowing me a kiss.