How to casually pitch woo after having thoroughly psyched oneself out?

i know, calling it "pitching woo" is an unfortunate start but i have to have a sense of humor about this.

oversimplified backstory:

• in my 30s, woefully on the neurodivergent spectrum, average-lookin', and been out of the dating game awhile

• have a distant acquaintance that i find attractive (friend of not-super-close friend group that i met through an ex a few relationships ago, i do not see this person out and about except at mutual friends' parties etc)

• asked a mutual friend about him and was given conflicting advice - first "don't date him, it's not a good idea" and then a day later "you should ask him out, he thinks you're cute" (when pressed for further explanation the mutual was vague and couldn't answer why the conflicting advice, and i haven't heard from her since lmao)

• whenever i've tried to casually make conversation with this person on social media, he was hardly receptive but also prefaced it with a disclaimer that he is bad at communicating, so that could just be a case of "i need to interact in person to get a read on them"

since i don't know the acquaintance well, it would feel weirdly forward to message them asking them out directly. however, since we are not super close, i have to really go out of my way to find an excuse to interact with them. that makes the stakes feel higher than they really are, since if it was someone i just casually ran into often it would make casual convo easier. as it is, if i want to see them i basically have to seek out events they are working/performing at which feels stalkery and frankly it's not even that serious since i don't know this person well enough to tell if they are actually a potential crush or just some random person i find cute.

how would you approach this situation?