How to judge when you should ask a girl out?
Literal language switch ON.
Boy meets Girl. He awkwardly and shyly avoids her whenever he sees her, because at one time he thought she was too good for him. Now he realizes that there is nothing to gain by thinking that way, and perhaps she is actually looking for a guy like him. It is certainly possible.
Boy and girl are in contact, but it is through internet means. Face-to-face conversations cannot be substituted. Boy needs to step up his... courtship process because he wants to make Girl happy and take her places. He now believes this is possible if he can program himself to walk over to her when he sees her instead of going into "avoidance mode", as he has previously done.
Hypothetically, after boy does this -- when can he ask Girl out?