Hi Else!
I was thinking about something I read about how popular people actually think differently than others. In social situations, they have a positive view of themselves, even when rejected. They tend to think the rejection was not about them personally, but about the other person. Or they don't see it as a rejection at all, but more like the person had something else they needed to do. As a result, the popular person doesn't just give up there, but will ask again later.
But when people have a negative view of themselves, they expect rejection and when they get it, it reinforces the negative view of themselves.
Plus, if you come across as someone who is really hard on themselves, others might pick up on that and think you are really hard on everyone.
It's just a social situation a lot of "raised as JWs" have trouble with, not having had a chance to start dating during normal developing stages as teenagers. Don't beat yourself up over it.
As far as conversational awkwardness, we all have that from time to time. The easiest way to deal with that is what everyone else said, show some interest in others. Remember what they said to you last time, without seeming creepy (ie asking about how a trip was 2 years ago when you saw her last). Lots of times, I feel so self centered when I forget to ask someone how their specific weekend plans went. I totally forgot about what they were so excited about and they tend to think I'm just a selfish bitch. Which I probably am. But when I watch other people, I notice they remember specifics about what someone was doing and they ask about it, which carries lots of conversations. Mostly, I think you just need to relax and other people will be relaxed talking to you.
Good luck with it! I probably will forget to ask you how this is going because I will have completely forgotten all about it in about 2 days. Sorry in advance.