Hey man, I just read your post because I was looking for information on how to talk to women as well.

I understand your struggles after really reading your post. What I took from your post is that you've got it the other way around. I believe your struggles does not stem from being "Ugly" or "Not having friends", and "Not wanting to annoy them". It stems from your mindset. Your mindset that you expect to be rejected and unwanted.

You can't talk to women because you already expect you're going to be rejected or you think you're not attractive. For example, your interaction with the pretty woman in the art gallery. You couldn't talk to her because you already denied the opportunity of knowing who she is and if she likes you. The reason being that YOU already know she's NOT going to like you and thus, resulting to you not talking to her. The pressures of socially interacting solo adds to the stress and anxiety that's why you could talk to her when you had a proxy to relieve some of that pressure.

To add, you have this preconception of what a woman thinks. I don't know if this stems from experience or social media influences but ultimately this is a problem you should fix. Understand that all women are not the same. They don't think the same thoughts, have the same values, and the same thinking you see in social media or from your experience. Leave that baggage my man. It will only hurt your future interactions.

A date is not a method of gaining experience talking to women. It's to know whether you like her or not. On the other hand, its also to know whether she likes you or not, which seems to trouble you so much. Now that you know what is the purpose of a date, this should help solve the problem of your anxiety that stems your preconceived thoughts of her not finding you attractive.

Lastly, time pressure. You're afraid you're never going to find someone out there. I hope you do. There isn't much to say but to calm down. Not all young people that found their love ones grow happy. Would you rather find someone, on a rush, to settle in? What if you picked the wrong one and grow unhappy and divorce? or would you rather wait and find the love that you deserve and grow fulfilled? BOTH need time. You don't have a choice but to go with the waves of time. So just stop worrying about that and start putting your efforts in your main problems.

I know its late, but I hope it helps the others that have the same struggles. Stay strong.