It’s worse than that. On two successive dates, one women got miffed because I tried to kiss her at the end of the date. On the second date, at the end, the woman got miffed because I did not try to kiss her. Talk about missed signals.

I have always errored on the side of extreme caution . . . . most women just do not get it. It is not worth pushing your way into something if the other person is not interested it in.

As women get older they start telling you what they want. HUGE benefit

There are studies about this that many men are programmed to think this way.
It really hit home when a gay friend of my late husband's INSISTED "you used to hit on me back in the day". No such thing EVER happened! NOT once! I was just "carbonated". I hated to take him down a peg but his tone was just SO shit sure that was the truth (in his mind!) .
And yeah, I pretty much had/have to be given a painted sign to know if I'm being hit on.

I can see how that finding can be very confusing and counterintuitive. I once wrote down a few tweets from an article entitled "Proof You are Not a People Person" and your post reminded me of a few that made me laugh. I will share 3 of them here since they strike me as instructive: "It's amazing how a simple act of kindness can change my bad mood into a suspicious bad mood." And "I get paid to be nice at work. Not sure why family and friends expect that for free." And "You call this an awkward silence, but I assure you, this silence is less awkward than anything I might say". Anyway, I honestly think your first move is to discover whether you are talking to an introvert or an extrovert. Flirting is not always a skill introverts are good at....either at picking it up or at expressing it.....at least this has been my experience. (And not to be too stereotypical but in the U.S. , southerners flirt more than mid-westerners... in my experience, so you have to take into account where people are from and their customs when meeting new people.)

My strategy is to just assume that everyone who smiles at me is actually making fun of me, laughing inside at my deepest insecurities they'd have no way of knowing about. That way I develop an unwarranted, bitter resentment against people who are just trying to be friendly, and don't even have to worry about potential flirtation.

10/10 would recommend.

That's why I'm always such a jerk, removes all doubt about intention.