I am ENM (41F), so I often see multiple people simultaneously and mostly date men.

At what point in dating someone (what time frame or number of dates) is it okay to ask for some things I need from them/the relationship? These men are interested in me, and I have gone out with them at least once. I am torn between not wanting to seem needy early on or feeling like I am "training" my dates.

Yes, I know some things aren't a good fit for me, and I break things off promptly. Where is the line? It feels like too much to ask too soon, so I say nothing and two months in, I am bringing things up (future requests, not in the past stuff,) and men are shocked and feel like I want them to change who they are. I mostly ask for better, more frequent communication (every other day texting between dates and upfront about expectations, things that bother you, needs, etc.) and feeling appreciated/feeling wanted/a compliment tossed my way.

Do I mention my needs sooner (it feels like I want dates to read my mind)? Feel folks out for a bit and then bring it up. Or find someone who more naturally does the things I need?