There's really no limit to how many women he can have a crush on at the same time, crushes are attraction, not love. Sounds to me like maybe he has a crush on #2 but knows he doesn't have a real chance with her. I'd guess, and I'm going way out on a limb here, that he'd be willing to give it a shot with #1 and before long might forget completely about #2 once he settles in with a real woman (no offense #2!)
Never undersestimate the power of asking a guy out, the #1 thing that attracts people is knowing there is already a strong attraction from the other person. Have you ever found yurself suddenly more attracted to a guy when you learn that he's really interested in you? Just joking ask him when he's going to finally take you out for the night, but then give him a look so he'll know that an answer is still expected! That always works well, because it takes the pressure of initiating things off him, plus lets him know he is not risking rejection, but you still don;t have to be the one to do the asking!