Why won't this guy ask me out?

Don't expect him to make the first move. If you left him, then you have to be the one who comes back. Otherwise, he looks like just some desperate ex who won't go away. That's probably why he hasn't said anything. Besides, you need to seriously think about why you left him and know for sure that it's no longer an issue.

You are kidding right? You broke up with him, you broke his heart, you know "he was very hurt when you broke up with him before", yet you still EXPECT him to ask you out and are wondering 'Hmm, why doesn't he ask me out'. I have seen many ballsy people in my life, but I think this is simply asking too much and simply stupid. You must be full of yourself!

Why don't you ask him yourself? Sometimes when you do the break-up part and sometimes don't wanna get hurt again so that might be it.