Awwww, that's a cute scenario. Awesome of you to provide a picture xDIf Ash saw May in an attractive outfit his reaction would be:
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Max: My sister is beautiful with this outfit, right?
Max: So you like her?
Max: So why are you blushing? you shouldn't lie
Ash: I-i need t-to train, b-bye
Do you guys think Ash will NOT be oblivious one day so he could try to flirt with May ?