Well, a lot of guys are still shy even though they don’t look like it. I know of quite a few who put off a lot of confidence but really aren’t confident deep inside. Maybe he had a bad experience before and he’s afraid, too. Guys can take a long time to ask out a girl because they’re scared even when it is unreasonable to be scared because there is always a doubt in his mind. Sometimes, the girl has to make the first step. Maybe he’s just waiting for the right moment or opportunity to come up. What he doesn’t understand is that the guy sometimes has to make the opportunity himself. More than likely though, he acts confident but is a little insecure (which isn’t a bad thing at all). Might I suggest bringing up an opportunity to see him or hinting at it in conversation?