>>53550921I read it a bit differently. I figured that because Misty's sisters never have to ask men out, Misty is conditioned against doing so herself.
Compare to Serena. Her female rolemodel is her mother, who is supportive, mature, and not very controlling. Daisy shows hints of being a control freak in the episodes spotlighting her, and she can get guys to do whatever she wants whenever. She never ever has to ask a guy out because they ask her out.
In Shudo's book Misty hadn't had a conversation with a male since third grade explicitly. That's a year to two years before meeting Ash. From her perspective it is just not normal for girls to take the direct approach