So, maybe I could just ask for some help venting about the hapless little comedy that is my sad attempts at steady romance? Maybe someone else can sympathise?

It’s really… it’s just tragic. Funny tragic. I’ve been doing, well, call it taking some inventory. On a lot of things. Things that I often try not to think about. This has turned up as one of them.
I came into my late teens with a skill set that’s useful for a lot, but not for relaxed socialisation. I also brought along a somewhat crooked sense of trust. There was this one girl that I sort of thought was interested. We went on a date, once. When I asked about a second one she said she was torn up about some drama with some other guy and didn’t want to get into something new right now. I backed off and nothing more happened.
Some time later another girl tried to ask me out for coffee. A couple of times. By this time I was so messed up, socially, that I couldn’t deal with it, so I dodged.
A few years later. A girl in a class I was taking seemed to come on pretty strong. And I discovered something about myself - I’m actively repulsed by girls that assume I’ll fall for sexy charms when I don’t find them intellectually stimulating. It’s not something I’m proud of, it’s just a fact that I feel insulted when a woman assumes that waving her eyelashes at me will make me fall for her. I stonewalled her.
Then I met someone. Someone… special. Really special. I fell in love with her. It’s not a memory I like revisiting. Turns out she’s lesbian. And also, it turns out that I need to be on my guard. Because if I think I’ve found a place where I can get some emotional fulfilment, I’m very easy to manipulate. Given that I’m fairly well off, with a nice car and apartment, that’s a lucrative and useful prospect for the savvy. I finally walked away from it.
Years later. I meet someone who’s in the same club as me. To me it feels like there’s some clicking. I try to make a few advances, but nothing happens.
Some time later. Same story, another woman: Club, clicking, nothing.
Somewhere around here. The girlfriend of a friend of mine started flirting with me. I stonewalled her and then spiralled into very dark thoughts about what I would do if I were given the launch codes for the US nuclear arsenal. And if I could just... I've seen people do what my friend's girlfriend did, more than once. Just, for ****'s sake, break up with the old one first. Please.
Another year later. I meet someone during work. By this time I’m so ground down in the romance department that I’m essentially reduced to an apathetic wreck, so I don’t really do anything. Instead she takes a sort of initiative, which results in us doing a sporting activity together regularly. Things seem good in a way I have never experienced. Up to a certain point. Then I must have done something wrong, because she breaks off our activities together and completely stops reciprocating when I suggest doing something together. Half a year later she asks about advice for the sport we were doing, because she’s heading out to do that with an old guy friend. I’m still trying to figure out why I was supposed to just be okay with being asked for advice like that.
Finally, another year. This time: I’m smart and funny and maybe one of the best people she’s ever met. Really, I’m just an amazing person. But it’s in the air that because I don’t share her religion, I’m sort of out of the race by default. You know how it is.

Damn it. Trying to talk about this is not fun. But I feel stuck. And I don’t want to be. Thing is, all of the above has left me with more than a sprained self confidence. Which in itself is pretty disorienting to me, since my natural state is a sort of easy going arrogant assumption that fear and hesitation is something that happens to other people. But beyond that, it’s left me not knowing the game. Just as a simple technical challenge, I have so precious little positive experience to use as a frame of reference that I don’t even know how I’m supposed to behave. The way I feel for the field of romance at this point is like being airlifted into an alien culture, where people speak a language I don’t understand. Honestly… I don’t even feel like I belong there. I mean, constant negative reinforcement is supposed to teach you something, isn’t it?