training social skills

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I guess I want to know whether what I have in mind is worth undertaking or not. So, I guess I want to know if anyone has actually tried what I am currently thinking of attempting.

I'm really bad with people, which I guess is common around here. I'm 38 and I wanted to spend the next couple of years focusing on getting better with talking to/approaching women. But, I seem to have a more basic problem. I'm no longer really interested in talking to people. Even my family or old friends. Usually any conversation feels forced and awkward and I think I don't have a really likable personality. I'm not interested in people unless I get into a state of being that is rare for me where I feel more normal/less anxious.

I wanted to spend the next couple of years approaching women and investing in learning to enjoy or be amused by social interactions. Wondering if anyone else has ever carved out time with that focus and had success as a result of that. Or maybe if you didn't have the success you were aspiring too, that would be interesting to hear about too. My barrier aside from what I've already mentioned seem to be anxiety, fear, a lack of confidence, and a very negative/cynical expression of self whenver I seem to open my mouth. I wanted a deadline for all this so that say I get to 40 I can see what results I got and how i feel about them and maybe just give up on this dimension of my life if I don't end up getting anywhere or feeling like my life is better as a result.

Thanks,

I had a bit of luck doing something similar a few years ago, and before I figured out that I'm an aspie.
It helped to meet someone that I found genuinely interesting, who also felt that way about me. She also made me mute, relatively, so it was almost impossible for me to monologue with her, and really challenging to say anything at all. (I actually walked away from her while she was in mid sentence when I finally asked her if she wanted to hang out sometime). But, once we actually got a bit of time together, it was easier. She was good at engaging me without overwhelming me. And she didn't seem to mind if, say, she asked me a question, and I gave some kind of answer, and then just asked her the same question. We also had a number of things in common, including working together. So we had things to talk about.
I ended up sort of misreading her. Thought she was interested in being more than friends when she wasn't, but we were able to make it through that as well.
I've had a few other experiences as well. Most of which were at least mostly positive. Some have been complete disasters. Some, I don't even know what happened.
And I'll start rambling from here if I don't stop.
But, yes. I think it's worth it. I can't really describe a method for it, but I'm still actively working on this sort of thing myself.

My opinion is that it is like getting in shape by exercising. There isn't any short cut. And helps to do all sorts of stuff that is similar to your goal but not actually the target. The problem with dating is that you want to carefully "read" the person you are talking to. And converse at the same time. This is much easier if you master the conversing part first.