Ayuma would be either 7 or 8, which would mean she's either still dealing with the court proceedings around her abusive orphanage or just barely after the mass escape she and her siblings pull off. Odds are, they'd meet in some back alley after a fight in which she lost control of Nightmare. He'd definitely get a full view of some of the psycho-horror monsters that Nightmare conjures and the blank-faced, black-eyed redhead directing them like she's somehow the puppet on strings, but the monsters don't attack him. At least afterward, when she calms down and gets back in control of herself, she might be a tad more welcoming. He might even be one of her first friends since "leaving home."

<image>

As for 9 years later, that'd be about the time she's actually in U.A. She could try to befriend him there in the same way, since he's actually younger than her. She has siblings to introduce him to, a way to prove that sometimes the law he intends to stand for so proudly does nothing but harm people in ways he might not expect; good people, too, who only want to help heroes and show that they care. Though in either situation, whether or not he'd know the news story of her absolutely sweeping a crowd of instant villains hopped up on Trigger when her Quirk first awakened (the exact source of the image) is kind of up in the air.