<human>: Give me the gist of the text in a nutshell

Somewhat contradictory title, I admit, so I'll try to clarify.

I have a bad habit of, after a night/afternoon of hanging out with a girl, becoming fixated on the question of whether she is attracted to me/interested/whatever. This is always following my not making a move, or trying to get closer (e.g. if we're watching a movie), or whatever physical action would be a more-or-less instant tell of whether the feelings are mutual. So, hence the fixation: I regret 'wasting' my chance, and am *unable to keep myself* from texting/calling said girl and asking her, in one way or another, that very question. 

Unsurprisingly this results in a solid "negatory," with the exact flavour of the response being dependent on the personality of the girl. I can't help feeling that I am blinding myself to the possible connections or even relationships that could've developed as a result of turning off every one of these people, whether they were attracted to me or not.

I should mention that the one girl who I did become intimate with (just short of sex; I'm a virgin) was what I considered 'just a friend' for probably about a year before things heated up between us. It was completely organic and unpremeditated, and although I wasn't attracted to her before we happened to spend a bit of time together, as soon as we were alone for a couple of nights things naturally moved that way. 

I guess what I'm asking you fine folks is this: how the hell do I shut off my brain (or turn it on?) and just trust that if someone is consistently showing interest in spending time alone with me then I can safely assume that they're interested, and try something? May be an issue with fear of rejection as well (definitely have a history of that) - I've made a lot of progress from being a person with very low self-esteem to recognizing myself as a handsome, confident, intelligent, and funny young man, but this complex/behaviour seems so deeply rooted in bad experiences which reinforce it that it is incredibly hard to shake.
<bot>: Baggage causing me to freeze up, then stifle the 'spark' by asking if the other person is interested. Similar experiences/advice?