@Chrissy90,
Sounds like a case of 'reversed friend zone', sucks doesn’t it? (sorry my cynical perspective kicking in again)
But seriously… (without knowing obviously either of you) nobody is a mind reader, people often read signals that are not there- or misinterpret them. With that said, the ‘Don’t ask yourself out’ (in my opinion) is a horrible concept. Personally I hate the run-arounds, the hints, the insinuations, the innuendoes, the expected, the ‘social’ norms. If you want something, get it…
Not to say, there isn’t a time/place for the above (or risks without them), but if you want real-time results with predictable outcomes… avoid them.