I'm a woman and I went through a similar thought paralysis for a while. Every time I met a man I would think, "Do I want to date him? If not, am I flirting too much? Am I sending the wrong message? Does he even want to date me? At what point do I set him straight about my intentions?" and on and on and on.
I'm an obsessive person, in general, but this was by far the peak of my obsessions. And a lot of things factored in to make a perfect storm of terrible thought suffocation.
As someone mentioned below, Cognitive Behavioral Therapy helped me with these unhealthy thought patterns (because obsessing is totes an attempt to control shit) and online dating helped me with the specific dating part. I dated for the entire summer, and nothing was long-lasting, but it sure stamped out my obsessions. Because, as stated above, I knew these guys wanted to date. And I knew that they (for the most part) wouldn't be unpleasant if I was honest about my conclusions after a couple of dates. It was great fun.
That was a few years ago. Now I'm still obsessive sometimes, and I still dislike ambiguity in dating. I just say how I feel and ask how he feels, because I know otherwise I'll fill in the ambiguity with fictional theories.
Polly, everything you write resonates with me. I seriously carry around a printout of my favorite parts of "How Do I Find True Love and Stop Dating Stupid Men?" in my coat pocket- just to remind myself that tepid can fuck off.
I just started seeing a guy who is not tepid and seems super great so far. I have a tough family history and I've told him some MyPast 101 stuff and so far so good. He didn't freak or interrupt too much. I guess my difficulty is that I'm excited/nervous to find out whether he's a good listener or not and that makes me want to TELL HIM EVERYTHING and see how he reacts. I'm working on being as natural as possible but not holding back. Oh dating. You're tough.