Jae
(Just to make it absolutely clear: (i) this is a *joke*, (ii) the two categories are not exhaustive, and (iii) it would be an extremely bad idea to do anything like this in practice, for all sorts of reasons)
Ryan Castellucci (they/them) 
@considermycat I did this (dressed as a woman for Halloween) in... 2010.
I'm nonbinary, not a woman, but still.
Esi@ryanc @considermycat ditto. I did this in the late 90's and early 00's, and now nonbinary.
With that said, depending on where the person is in the "exploration" phase I would say offering transition info could put them into defense.
I would probably rather just compliment their outfit, etc... Give them the possibility to swim in some gender euphoria. <3
Three LLMs in a Trenchcoat@considermycat so drag queens are shitty now? I wouldn't know
Chasnah
Alex, the Hearth Fire@me @considermycat do you really think most drag queens would say they were a girl for Halloween as a joke
Sparkwave@considermycat Also, if it's a femboy, they will probably not mind, and just find it amusing
Hippo 🍉@considermycat lol for the second part
Gender David Copperfield@considermycat this is why our 21st transition anniversary is next week.
Shyra& 🐍 🌘Me eight years ago, cosplaying as Katniss Everdeen…
Richelle SparrowWhen I was much younger, in the 70's and 80's, Halloween was the only time I could explore being a girl. It only took until I was in my mid-50's to go full-time.
Julia :v_bi::therian:@considermycat thinking about the time I wore a maid outfit as a Halloween outfit while I was still pre-medical-transition
Andreas, DJ3EI, he/himGiven the overall civility of the Fediverse audience, I dare to assume the transition info will be offered in a friendly way.
If so, other people, e.g., non-shitty normal cis dudes, will not be offended.
So it's win/win/🤷.
kira :3@considermycat i think if a really buff girl like in that pfp gave me information on hrt i would become a girl instantly
@considermycat i mean i already did that last part but still 
Pamina@considermycat Pissing off shitty cis dudes is also a great way to get yourself beaten up, unfortunately.
june@considermycat jd vance did this at a halloween party
Peter Brown@considermycat bear in mind that cross dressing at Halloween was part of the festivities for the old Celtic New Year and some of that tradition has moved into the current New Year as pantomimes and first-footing