Sick of not knowing what to say

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I hate trying to make conversation with people. I just don't know what to say. Nothing comes into my head. I hate trying to lead a conversation especially if the other person is not very talkative.

I can't just go up to people and talk away. I sometimes look at people talking (especially someone I want to talk to - read guy I'm attracted to) and wonder what they can find to talk about.

I hate how my brain works in such a way that conversation is difficult for me. It makes me feel very isolated.

I've been the same way my entire life. When I was younger I was really bad, it took me ages before I ever had a halfway normal conversation with someone. Now, I have gotten much better, and only struggle in certain situations.

What I do is have several "go-to" things that I can talk about, with anyone. If I do something interesting on the weekend, or go to a good restaurant, I will ask them what they did and then tell them my experience. I try to think of questions that I can ask someone...I find that questions are a good way to get them to talk so you don't have to! Also one thing I've noticed with a lot of the big talkers: they repeat themselves constantly. There simply aren't that many things to talk about out there, so the people who really talk a lot just say the exact same thing over and over again in different (and sometimes not so different) ways.

It is usually pretty easy to keep someone talking about themselves. Oddly, afterwards, they think that they know you better. Sometimes, as they talk, you will remember a similar story. Sometimes, that is a good thing for you to talk about.
Once you have talked to someone a few times, you should be able to remember what they were worried about last time, and can ask how it worked out.
There are many people who talk a lot, and barely notice what you say. If they ask how you are, and you use the usual intonation for "Fine thanks!" with "Fairly Suicidal" they won't even notice, but there is not much point in listening to them except as a favor.
Teenage conversation can shade off into a stylized ritual around certain stock phrases. It is usually safer to quote than to compose if possible, so don't over-think it.

It is usually pretty easy to keep someone talking about themselves. Oddly, afterwards, they think that they know you better. Sometimes, as they talk, you will remember a similar story. Sometimes, that is a good thing for you to talk about.
Once you have talked to someone a few times, you should be able to remember what they were worried about last time, and can ask how it worked out.
There are many people who talk a lot, and barely notice what you say. If they ask how you are, and you use the usual intonation for "Fine thanks!" with "Fairly Suicidal" they won't even notice, but there is not much point in listening to them except as a favor.
Teenage conversation can shade off into a stylized ritual around certain stock phrases. It is usually safer to quote than to compose if possible, so don't over-think it.

I used to hate to make conversation. Whatever I had to say was usually not very on-topic in any conversation.

What I do now is tell jokes. I usually have two or three recent jokes to tell and tell them to everyone in the hope that it passes as conversation. And it usually works. Generally I tell someone a joke or two, listen to them tell a joke or two if they have any, and then leave. Works great.

On the other hand, when pulling up to go into a place such as the local Dairy Queen, I've seen people look out the window and see me and get up and leave in a hurry before I can come in and tell them any jokes. So I guess that it doesn't work that great. It doesn't bother me, though -- I just tell them the joke the next time I see them.

One problem is that I often have no idea who people are because of prosopagnosia. I will know that I should probably know them in such a relatively small community and so I act like I do know them. This usually works pretty good -- people who it turns out I didn't know usually just think it's a friendly town.