Miles / Gwen
They were definitely way in over their heads and out of their element. Gwen knew that, and really she probably should've just asked Tony for money but that was taking the easy way out and they were old enough to be independent, right? Sure. Maybe. Probably not. But they were doing it anyway and if they got caught, well, it wasn't like they'd never been in a pickle before anyway.
The thing about gambling was, sometimes it was hard to know when to stop. Gwen was finding out first hand that after winning once, she wanted to win again. "Do it again!" She encouraged him. They'd made ten extra dollars. And soon that escalated into fifty extra dollars. One hundred extra dollars. Five hundred extra dollars. "Dude! We're gonna be able to ride that roller coaster like ten times and probably hit up a buffet afterward. Keep going!"