Ok bear with me. I like to joke that a significant portion of my music library is white women with guitars. I listen to a lot of art pop/indie, basically. Phoebe Bridgers, Boygenius, Fiona Apple, Weyes Blood, Angel Olsen, Aldous Harding, etc.

So where are the black women with guitars? I think that singer/songwriter trope of a woman with a guitar (or sometimes a piano) is traditionally pretty white, so what artists are you aware of that break this trend? Closest I've found so far is Kara Jackson, who I would highly recommend, by the way. Not too strict about genre here, so whatever you got is welcome.

Tale as old as time, I suppose. Straight man doesn't understand women. I'm hoping this site will provide a healthy place to discuss my feelings and get wholesome input from others without it turning into a pity party or cesspool.

I didn't have any interest in dating until after I'd graduated college. Unfortunately, I immediately moved to an area of the country notorious for its unfavorable gender ratio. There are many more men than women here which means I'm starting on hard mode. I do at least have some traits which make things easier than for most. I am high earning, reasonably fit (not super cut but I work out most days), tall and I believe mentally healthy. However I can tell that my approach doesn't really catch with most people.

I've had limited success out here. Some of my failures are mine to own. Getting started from nothing means I'm venturing into the unknown. I'm a naturally anxious person and never felt any intuition in social situations. Thankfully I've managed to figure out a way of being that jives with some people and learned the hard way the things I do that don't jive so well. But dating seems to have its own social rules - and they're harder to learn due to all of the misinformation.

To sort out a lot of the misinformation I look to the people I see with the greatest degree of success. The older couples that are clearly deeply happy. My parents do pretty well in that regard. They've been married for 30-ish years with nothing more than a short argument between them. Or maybe I'll talk with an older co-worker who loves his wife the same way he did decades ago. People say that all happy families are the same, and unhappy families each broken in their own way. It's clear that there are some things in common with the happy couples - a universal recipe for happiness and success.

• Forgiveness
• Consistent effort
• Flexibility
• Similar values

I try to take these virtues with me when dating.

Of course, mutual attraction is a black box and also plays an important role. I've tried dating women that are just outside of what I would consider attractive. I think it's important to know what truly is important to me. But I found that things did not feel right and I can't compromise in that way. I'm not looking for a 10. But if I know they are not attractive to me it won't work.

In the normal world (outside of online dating) I think the odds of a random person being instantly notably attractive are very low. Someone needs to be sufficiently aesthetically attractive, but also have the right mind and soul. Without the latter two I have no interest. So for me when I've met a nice woman from a dating app the process of learning more about this person begins - and it can take a while to truly get to know someone. But I draw on the virtue of effort and am more than willing to make that an active process as we get closer.

There are actually some people out there that this all seems to align with. I think it's mostly a matter of time before I find the right person - so I'm not entirely discouraged. But the vast majority of women I meet seem to have the same feedback. They don't feel a connection - maybe that translates to "they're not attracted enough to me", maybe it's something else. But what I call a "connection" is something that can't be absolutely determined after one date.

Given my profile pictures are representative of my appearance, I don't think they're all saying I'm aesthetically unattractive to them. Sure, some might decide after meeting me that they aren't as attracted in person. I experience that for myself some of the time. But I suspect that much of the time this is more of a mismatched approach. I really want to know either how better to find my kind of person, or what ways I can adapt to be flexible for the women I'm dating.

Edit: Thank you everyone for your thoughts!

A lot of people said a lot of things, many of which sounds right to me but only a few I think are applicable as next steps.

1. My own reflection leads me to believe that being more present and less analytical will make dates more enjoyable and productive for both people.
2. Keeping a very long term goal in mind cripples the dynamic of early dating. It requires future prediction abilities beyond what a human can do.
3. I don't know if I can be the "fun guy" all the time but I can definitely increase the amount of fun.

I wrote up a journal entry about what I wrote here and everyone's responses. I'll bring up my thoughts with my therapist later. Maybe this is weird but I threw the journal entry into ChatGPT. If nothing else it was positive and cheerful, which is helpful. But I was able to drill down on a few different things and got answers that sound reasonable. This is surely a common enough topic that it's got good training data for it.

I'd also like to say, for whoever reads my comments, that much of what I wrote is more about following a thought as far as it will go more so than putting my internal constitution into writing. I'm here to be as malleable as I need to be.