I think what was meant was asking this: "Did you enjoy all of those dates that you went on, with all of those different woman?" Because if there are some which you didn't really enjoy or show interest in (because really now, we all have times where we're interested but do a poor job of showing it! - I certainly do!) then you have to make sure you discount them when you're reflecting. Because the woman would have almost certainly noticed it and of course not respond.

That would then leave just the women whom you were interested in and enjoyed your time with. Is there a chance that you've miscommunicated with them, like sent them incorrect signals or possibly misinterpreted theirs? That might be something to look at for yourself.

If you feel highly interested in someone, how do you let her know that? Not just during the date - but afterwards? Unfortunately there is still the stereotype for the man to take the initiative on stuff, so if you haven't proactively messaged her or attempted to initiate another plan or at least more than a superficial conversation, then she may think that you are not interested and give up.