My last relationship lasted fairly long (almost 8 years), but it's been a few years and I've tiptoed back into trying to date over that time. A major part of my problem is that is get into my own head lot, and I put a lot of pressure on myself.
It's not that I'm uncomfortable with dating and am forcing myself. It's more that I recognize it's not often that anything comes up. I've moved to a smaller area for work (and can't readily move until at least next summer), so numbers aren't great. It's also heavy "country and proud" crowd here who prefer stereotypically masculine men, so I'm not the much of anyone's type and the local crowd isn't my type either. On top of all of that, even in the best circumstances it's somewhat a rarity for me to meet someone I click with and am interested in that way. In the 3 years I've been single, I've only really met 2 people who I liked. With the current living situation, it adds on to make things harder to been attempt meeting people.
So what happens when I do is I get more nervous than I already am because the pressure feels more intense? If they say no, that's fine, but I get anxious because I know that that means it's very likely that it could be a long time before I meet someone I'm interested in again. On top of the general nerves because it has been a while since I've actually asked anyone out and I wasn't exactly great at that before. Which is stupid, but that's just how the brain works, and so it sends me into the standard overthinking mode. Which makes me just not say anything or make any move at all, and that gets things nowhere.
I've started thinking about it because there is someone I like. We've run into each other quite a few times at conventions, and at this point we usually stop and talk for a bit when we recognize each other. she even folded me into her group one time when my friends had all decided to head out early. She's my type, very kind, and we have a lot in common, and I'd like to at least try. There's a big con this weekend and we'll likely run into each other. I just want to ask if they'd want to go to one of the events at the convention or maybe hang out sometime outside of the convention, but I'm worried that I'm going to overthink it, clam up, and say nothing more than my usual friendly banter. I'd rather get a "no" than a "what might have been" and I'd definitely prefer to not spend the rest of my life letting anxiety in the moment stop me from actually taking a chance. So does anyone have good ways of minimizing or coping with the overthinking that comes with the nerves?