Are people normally this confussing when you are asking them out?

[CapnAwesome]

I wouldn't ask a third time, personally. Being a girl myself, if I was interested I would have said yes the first time. The second time was fine to ask, just to be sure I guess.

But at this point, if she decides she is interested in him, she will reach out to him. She already knows he is interested.

It isn't fun being asked out and having to turn someone down. I wouldn't make her have to go through it a third time.

I'd normally agree, if she flat out rejected him. But she said "I'll have to think about it" that automatically leaves the door open. I think "hey, have you given going out with me any more thought?" is appropriate. Then you can get a more clear answer.

Btw, not that this is relevant to this case, but in many countries a man is expected to ask a girl out multiple times before she says yes.