I really hope it works out for you that way.
But I've been working as an IT professional with Wall St firms since I was 21.
That's 36 years!
And never once have I had a girl I find attractive show attraction towards me.
Hopefully things are different now for you younger guys.
I really mean that.
I would love to see younger guys who are like me do well with females.
Even though that ship has long since sailed for me.
I hope it does too, I wonder where I could have been, and what I could have had, if I just graduated on time and didn't let my mind take me off course.
However, I would have had to have understood how all this works, and fixed my thinking a long time ago. Otherwise I would have been in a job, and still thinking the same things I was thinking in my teens and 20s, and with less free time to figure out that it was wrong, and to figure out what's right instead.
I don't think there's anything wrong with your job. It's, as you said - solid, upper-middle-class work. Some might even say upper-class, depending on who you ask. From what you've described it sounds pretty good to me. There's nothing humiliating about it, and to me that's the most important thing.
It took me a while to get it but I came to the conclusion that I too, am suited for knowledge work/office work. I'm more suited to that than the trades or the military, I don't have the body or coordination for that. I was never a genius, but I've always been stronger academically than physically. If I could get into mental skilled work, then pursue some kind of cool skill outside of work to be an interesting person, then I think I'd have a chance.
Honestly, I think it's the women that you're going for. It sounds like you're going for women more based on looks than personality/emotional compatibility. These women all sound like the egotistical type, that would normally go for the egotistical guys, because that's who they are compatible with, that's who thinks the same way as they do. And I don't say that to attack you, I say it as someone who thought a similar way for a long time, until I realized how and why it just doesn't work, or is so unlikely to work, that it's not worth the misery you have to go through. It took a while but I realized that the women I wanted to have sex with the most, were usually not people I wanted in my life the most, or even at all - not people who thought and felt the same way as me, not people I could see myself caring about emotionally, or even people I liked that much as people. They just had hot looks. Outside of the bedroom, I wouldn't even really want to hang out with them that much. And I realized if that is the case, it's not worth it then. It took a long time for me to realize it, but the most important thing to me, is someone interesting, someone who makes me feel good to be around them, and someone I can see myself caring about - an authentic emotional connection. And in time, I find that physical desire that might not have been there to start with, can grow from that.
Just my thoughts, anyway.