Livre d'Or

Lots of ideas there, and I'm in a rush so I'll just respond to what I have a straightforward response to:

Yes, "loneliness" absolutely encompasses a number of different feelings. As a bit of personal anecdata, I frequently feel lonley - though I don't ascribe this to unfair-universe so much as I do to geography - but there are distinct, different, feelings for (a) Too long without good friends who I can be myself with; (b) Single too long; (c) Celibate too long
(I don't really count the last as loneliness at all, but it does sort of complete the set)

I think there are lots of things that I could say that are relevant to other bits of your post, about cultural issues around Western courtship behaviour, which I think is a fucked-up mess, and which may be harder on men than women in some contexts but is mostly probably just Bad For Everybody, and especially bad for anybody who isn't good at reading body language & subtext. But all of this would require careful nuanced thought and expression to avoid coming across very badly, so I'm not actually going to try here.