My problem with relationships and age

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Yep. I’m just one person on the Internet, too.

Your tendency is to adopt the negative opinions as true—and disregard any deviation from that—even though the deviation could very well be true.

In my experience, people dont look askance at relationships with a ten or so year age difference.

I'm not concerned about what people think. Its that there's a reason they think it in this case. If I wanted to jump off a cliff and people said its a bad idea, would you all be telling me I shouldn't worry what people think and just jump?

Age gaps relationships are typically predatory. And when they're not they're transactional, ie old rich man giving a young beautiful women money and expensive gifts in exchange for sex. It might be less obvious, but 45 year old man who offers more financial security that a 25 year old with a 23 year old woman who is more fertile than a 40 year old is still just as transactional.

Question is: why would a younger woman want me anyway? Why would anyone choose a socially awkward broke overweight loser over someone her own age?

Yes. This is something I keep saying: many women find me likable, but they're all either married or only interested in me as a friend.

It’s time for you to give up on the idea of dating someone younger than you.

You may find women around your age who still look youthful.

But yes, you are right… a 20-something woman is very unlikely to go for an average 40 something.

yep, the consensus is
1. Work on negative cognition (seek professional help if possible otherwise use online motivational self-help resources)
2. use positive thoughts to motivate
3. use motivation to exercise/diet
4. use improved self-esteem to train/retrain
5. use training to get better employment
6. use better employment to get higher pay
7. Stop remorse over age as that's something you can't change

The brains trust can't really advise you further

You still did not answer what you do to/for/with women to let them know you're interested in them romantically.

I've been told in the past by a girl who liked me that I just didn't give her the signs and respond to her. I was playful with her but I guess too shy for her to be sure. She went on to date my best friend at the time and that wrecked a lot of things.

the less-than-spoken question has not even been remotely answered, like how does one decode the secret signs they are interested in one?

We're expected to it all the f**king time.