Aquilaruspante,

Out of interest, are you only meeting women thru online and social circle/work? I would encourage you to at least try cold approaching, if you're not already doing so. It will open you up to a whole new pipeline.

It sounds like you're over-thinking things and going way too much into future projection. Whilst you can obviously joke about these sorts of things to women (and is a useful technique to seed future plans), I wouldn't get serious unless you're actually dating them.

Z