I've lived in the Midwest before and it's worse there, partly because I couldn't practice my sports which kept me out of shape, partly because it was even harder finding like-minded friends, in part because I don't like regular sports. I would definitely consider moving out of country if that opportunity ever came up.
> And women don't want a man that they have to "guide" anyway. They want to attach themselves to a guy who's got his sh*t together and knows what he wants.
This leads into what I consider unrecognized female privilege. From what I can tell, women have a pretty big list of superficial expectations from their partners, and are really quick to dismiss those who don't fall into place. They also gave an abundance of interested suitors who they can sort through until they find they one they way. Me on the other hand, I'm lucky to find someone interested in me who even passes my most basic tests.
Equality in dating doesn't exist and it's highly skewed in favor of women.
The issue is likely that you're not very attractive or you're setting your standards too high for the women you pursue.
As for standards, why should we settle for less than an equal version of ourselves? Same height, education, looks, strength, ability, finances, etc.? In my experience, women almost exclusively "date up".
I'm athletically fit and don't have any intentions of bulking up. I'm at the climbing gym a few times a week, and climb outdoors a few times a month. Multi-pitch, trad, free-solo, whatever.
The biggest challenge, and the entire reason I started commenting here, is that finding friends is hard. Chatting someone up is easy, but getting a new person to take time out of their schedule to hang out with you is really difficult.
But the confidence benefits were huge enough that my dating life is actually a lot better. I only online dated before then, and after, I can go to (queer) bars and pick up girls and bring them home. I still have the problem that I mentioned in my other reply, that it's really hard to get people to stay (I say "people will go to bed with me, but they won't wake up with me")
I don't think you're transgender (and if you are, that's a separate discussion), but the lesson I draw from this is that you are better off if you maximize the things that naturally interest you rather than trying to be someone you're not. Snowboarding and rock climbing are both great contexts to meet people in. If you are confident and in your element there, you'll probably attract people much better than if you put a lot of effort into trying to be someone you're not.
I also have the somewhat receding hairline which is a lot more unsightly on a woman than a man. I had a couple consults over the last couple weeks about hair transplants, actually. Usually I wear berets. But nobody else is as bothered about it as I am; the hat always comes off when I bring someone home.
If you put a certain energy and intensity into the world, people will see it and not the other more minor things. If you're reserved and unconfident then they'll see more of the rough details. If you feel "aimless" as you've said you are, people won't see the energy you put towards the things you love, they'll see that instead.
Some people are born confident and attractive and never had much reason to question it. Some of us really had to work for it. But the answer wasn't PUA stuff (I spent a decade trying that), but transitioning and really embracing who I am.
Are you in the US? Leave it. Seriously, I encourage all men to become expats if they don't already have children in the US that they are trying to raise. Just completely abandon a system and society that is failing to meet your needs. If you feel inadequate, ask yourself A) by whose metrics? and B) why?. Go to the gym, dress better. Have goals in your life (outside of dating) that you aggressively pursue. The US dating scene is increasingly insane, and men don't even realize it because they aren't exposed to kind, helpful, friendly, feminine women that are simply abundant in other cultures (or even in Flyover states, if you look there).
And finally:
> there isn't a lot of guidance from women
The more women you date, the more you will realize that most dating "guidance" from women is absolutely useless. The cognitive dissonance most of them have will blow your mind when you witness it first-hand. And women don't want a man that they have to "guide" anyway. They want to attach themselves to a guy who's got his sh*t together and knows what he wants.