I have a few big issues with first dates:
What to talk about..... I have no problem talking in general and asking questions. But one thing I tend to do is purposely not go into topics I don't want to talk about. Things like sports, or travel, or outdoorsy things. I simply have no interest in this stuff and its incredibly awkward to talk about it since its always in a negative way. Its a mix of being honest with things and having limited interests. You dont have a lot to talk about positively, and the things most others enjoy which I don't, I only know how to state my opinion of it...TOO honestly.
A great example... if the topic comes up about online dating (where we met) they tend to ask how long I've been on it. What am I supposed to answer? The truth.... over 3 years? Girls really don't want to know in 3 years you can't find someone. Or lie and make something up on the spot (not easy)?
And most girls don't understand the disinterest with being social. I don't have many friends around to do things with these days and when I do go out for something its not with more than 1 or 2 people. I HATE parties, and I don't drink at all. Girls hear this and they tend to run away screaming. How do you get around this sort of thing? Other than play the numbers game till you find someone similar.
The other big issue I have is how do you tell their interest? Most never do anything obvious enough to pick up on. So I go the whole night wondering if they're interested, if they'd like if I held their hand. if they'd like a kiss, etc. Basically, unless they more or less made some sort of 1st move, I'm way too shy to. And since I would never try to push anyone to do anything too quick, I have no reason to try and force it, I'd rather wait it out. But I wonder how many times I've screwed it up because I was too shy, and they took that as though I wasn't interested in them.
I've been wondering if I should mention something along the lines of being shy and AS/SA before we meet so they know how I might come off, but that seems like a red flag to most girls.