It may be that both are thinking in terms of considering the other person. People use their self as a reference point. When you try to model in your head how so

It may be that both are thinking in terms of considering the other person. People use their self as a reference point. When you try to model in your head how someone will take your request, you may be thinking in terms of how another asker would take being asked a request. In that case, you would think that the other person would be fine with it, since they're just as comfortable with asking for things that have a low chance of being granted.