Having been where you've been, may I suggest that the dealbreaker is that you're treating dating like a World of Warcraft inventory checklist? I wish someone had told me that when I was saying the same things.
FWIW, I do think there are similarities between dating and RPGs that I wish I had understood before
* you can improve your character: confidence is important, if you feel ugly sometimes you can do stuff about it (i.e. go to gym). Ditto if you are a boring talker, or if you are a poor listener.
* grind. If you are, like I was, a guy that has a couple hours on a weekend to meet a new possible date it's hard to find the "right" one. Try to increase the chances (go out more, frequent new places) and do try more.
This is fair enough and true. Back when I was in my early twenties and late teens I used to grind all the time (going out to bars and talking to women). And although I experienced more than my fair share of rejection/disinterest, I achieved plenty of success and abundance.
These days I am just lazily sending out messages on OKCupid. And when I do go out to bars, I almost never approach.
* you can improve your character: confidence is important, if you feel ugly sometimes you can do stuff about it (i.e. go to gym). Ditto if you are a boring talker, or if you are a poor listener.
* grind. If you are, like I was, a guy that has a couple hours on a weekend to meet a new possible date it's hard to find the "right" one. Try to increase the chances (go out more, frequent new places) and do try more.