Is it purely a numbers game though? Most people have this thing nerdy academics call a 'mate value sociometer' and they use it to help decide how hot a female to pursue. Of course, this sociometer has to be calibrated, so you really want to be rejected often enough to know where you stand. My point is, it might be better to keep this sociometer in mind (especially since non-neurotypicals tend not to have this instinct), to at first target your proposals to be as informative as possible, and then later on target those girls your mate value can buy. (this is in fact what studies have found neurotypicals to be doing)
It's not purely a numbers game. However, it really helps if you can interact with a number of people that's at least in double digits.
Get used to meeting new people. It's good for you. You grew this great big brain to do chimp-chimp interaction better, after all - you have an aptitude for this sort of thing. MEET MORE PEOPLE!
I am beginning to suspect that it is surprisingly common for intelligent, competent adults to somehow make it through the world for a few decades while missing some ordinary skill, like mailing a physical letter, folding a fitted sheet, depositing a check, or reading a bus schedule. Since these tasks are often presented atomically - or, worse, embedded implicitly into other instructions - and it is often possible to get around the need for them, this ignorance is not self-correcting. One can Google "how to deposit a check" and similar phrases, but the sorts of instructions that crop up are often misleading, rely on entangled and potentially similarly-deficient knowledge to be understandable, or are not so much instructions as they are tips and tricks and warnings for people who already know the basic procedure. Asking other people is more effective because they can respond to requests for clarification (and physically pointing at stuff is useful too), but embarrassing, since lacking these skills as an adult is stigmatized. (They are rarely even considered skills by people who have had them for a while.)
This seems like a bad situation. And - if I am correct and gaps like these are common - then it is something of a collective action problem to handle gap-filling without undue social drama. Supposedly, we're good at collective action problems, us rationalists, right? So I propose a thread for the purpose here, with the stipulation that all replies to gap announcements are to be constructive attempts at conveying the relevant procedural knowledge. No asking "how did you manage to be X years old without knowing that?" - if the gap-haver wishes to volunteer the information, that is fine, but asking is to be considered poor form.
(And yes, I have one. It's this: how in the world do people go about the supposedly atomic action of investing in the stock market? Here I am, sitting at my computer, and suppose I want a share of Apple - there isn't a button that says "Buy Our Stock" on their website. There goes my one idea. Where do I go and what do I do there?)