Milestones of Moving On (?)

[TJT]

So I actually have a straightforward question for once, hah.

Last month H did transfer me his portion of what I pay for our combined insurance. He did it without me prompting - we texted about it briefly before and then the following month, he did it.

This month I have not gotten it yet. Perhaps he's just working around a different timeline this month (I failed in that we never did set a specific date for the transfers to occur, I just said once a month) but my question is what to do IF he doesn't transfer the money this month?

Do I initiate contact and ask if he can send it? Or not if, but when? Or let it go because I don't want to look needy and/or put pressure on him? Kinda goes back to questions I had really early on about if his "thing" is that he needs to feel valued and needed, but it's bad for me to appear needy, how I reconcile those two things in the actions I choose.

I guess ultimately me asking him for money for something that he is responsible for anyway and that I'm just continuing to pay for because of our legal status is not me being needy... it's holding him accountable. But still puts me in the same situation, because holding him accountable seems like more of the same and I kind of see me NOT saying anything to him as a 180, in the sense that he knows what his responsibility is and I really don't want to be that enabler that's always chasing things down or sorting it out. And aside from him knowing I want/need it, there's not really any other consequence to him if he doesn't pay. I can't force him. I can't charge him a late fee. And me expressing frustration about not having received it doesn't seem like a consequence that would be beneficial to the sitch, right? It just seems like the "best" things to do in this case to achieve various things contradict each other... so need advice!