Riley would tragically not believe she actually meant to ask him out because she "like liked" him, and self-sabotage the whole thing.
He would ask her out, never. Never ever ever. But assuming he ever reached a point in his life where he was mentally stable and confident enough to try it would basically be like "hey, do you want to like, go to the movies or something this weekend?"
Leia would ask her bigger crush out something like "Hey want to go get dinner?" and he would not realize she was asking him out, agree, and then she'd be like "No, like a date." and he'd then be like "oh..." and they'd have to have a long conversation about this sudden development lol.
If she asked her other crush out, he'd probably want to take charge of the whole affair, turning it into something completely different from what she originally intended and it would be a big mess...
If her bigger crush asked her out, she'd be happy, tell him she liked him too, but apologize saying her head is a mess right now, and she's not ready to date him yet. "She'd not be what he's looking for." allegedly and say something like "I don't want to waste your time."
If her second crush asked her out, she would probably say no at first, irritated and flustered, but then let him persuade her into going.
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