First of all, sorry for not replying for such a long time – I’ve had a really busy last few days (mainly because of work) and I’ve been kind of worn out. I’ve also been trying to think about what you’ve both said. I want to make sure I’m giving proper answers to your questions. I just wanted to say that I haven't been ignoring you (or your questions); it's just taken me some time to respond. Thank you for your responses too.

I don’t focus excessively on relationships/being single, because, well, that’s common advice when people talk about relationships – if you want to meet someone and if you don’t want to be alone, you can’t focus too much on it. You have to go on living your life and sorting yourself out and then, eventually, you’ll meet someone who’s compatible with you. So I do that. I do stuff because I enjoy it; I keep in touch with current friends and try to make new ones. Keeping myself busy is all well and good, but, as you say, the day/night/week ends and you don’t have anyone to go to/with. It’s just a bit demoralising sometimes, especially if you know lots of people who are in relationships (whether they’re overly couply or not, it still reminds you that you are alone).

I’ve occasionally fallen into the trap of going out/hooking up with someone, with whom I’m just not compatible (I’m sure a lot of people have). Obviously we know it’s not sensible and it barely ever works out for anyone (it never has for me), but, as you say, we do it because we’re desperate and/or tired of being alone. Like you say, sometimes we just get tired of trying. Being alone can be bad sometimes, but trying something with someone and having it not work out can be so much worse, so, playing the odds, it seems better to deal with the low-level sadness, rather than risk the absolute lows of rejection/feelings of incompatibility.

Hmm… Interesting question. The answer is probably both, but I’m not sure whether those two are independent, or if one causes the other, which perpetuates the cycle. I’m always worried I’m not keeping the other person happy (I’d have to keep asking questions like “Are you feeling alright?” “Are you having fun?” “Do you want to do something else?” etc) I’d just worry about making someone do something they’re not comfortable with (although, given most of the people I’ve been with, they’d definitely say something). Of course, it’s good to make sure the other person is at ease with whatever’s going on, but I feel I ask more than most people do (just a feeling).

As for keeping myself happy, I probably just keep overthinking things. I’ve been single for such a long time that, in the event I do actually meet someone, I’ll get stuck in a cycle of thinking either the person doesn’t like me, or convince myself that they aren’t a match and things won’t work. I know I shouldn’t go in with such a defeatist attitude, but it’s tough to stop. But it’s also true that sometimes you go out with someone and you don’t feel anything/there is no chemistry between you, so how am I supposed to tell the difference? Do I not feel anything *because* there’s no chemistry, or do I not feel anything because I’m just internally worrying myself?

I feel that some of this is conjecture. Some days/weeks I feel I have a concrete idea of why this makes me sad, but then that certainty goes away/changes. I just worry. Maybe that’s my thing. I need to correct this before I can make progress, but I don’t know how.