How to ask him out?

How long should I wait before I ask someone out?

• Okay, so let's say a lot of the women I know have boyfriends and I don't know too many women who are single (as far as feeling okay about going out on a date with me) except for the occasional woman walking down the street, minding her own business and being someone I don't even know. In other words, the idea of "just ask one of your friends out" would be a good idea if I knew a friend I could ask. Anyway, people do make connections one way or the other, even if it's an impulse situation. For instance, a cashier at the cafe might smile at me and say hello and I don't know if she'd want to chat and perhaps go out on a date. The same thing could be said about a woman who passes me by on the sidewalk and smiles at me. My question is: when should I ask someone out? I'll make this multiple choice if you want to answer that way. A: Ask her out right when you first want to, even if you never saw her before. You might be surprised and she says yes. B: You ask her out after having talked to her a couple of times previously so at least you're familiar enough with her, but don't wait too long after. C: You ask her out if you've known her for quite a long while and you now have made the trust happen so she won't take it the wrong way if you ask. D: You wait for her to ask you out or at least after she has made the first move. You might offend her if you make the first move.

• Answer:

  B and C are the best choices. It depends on the type of person you are. You can't just ask a woman on a date by just smiling at her. You have to be bold to do that. And C is also good considering that you know her for a while.