should a person contemplating becoming a rabbi go out on halloween?

i am becoming religious now, i am in middle of the process, i was sorta wondering, i see a few movements, i see the litfish, i see the chasidim, i see chabad, but the only thing is, chabad looks appealing cause of their warmth, but i keep on hearing that they have this extremism in messiah and its against jewish law their beleifs, is it right to go to such a movement, or better just go somewhere else?

I would like to know the proper answer to a Conservative five-year old who wants to know why he must wear a Yarmulke (to Hebrew school) while his female classmates do not. I am a Frum teacher and understand the answer on more advanced level, but am having trouble coming up with a way to explain it to my students. Thank you for your time and consideration, Sara Pollak