He's not the shy type, having really spent most of his existence clothed in speed... and he admires her form, so he figures he has nothing to lose with the movies, even if he might occasionally be hard pressed to pay attention to the screen.
"If you wear the corresponding female costume to whatever you pick, you entirely have a deal."
Because that's just fun... and this way, he doesn't need to know pop culture to pick out a costume if he loses. Besides, he's almost positive she'd go for something classical, rather than raw humiliating, just to see someone do it.
Which gives him an idea. "And if I beat the obstacle course in less than 11 seconds... I then need to do it a second time, in the same state of dress, but you need to do it with me, we'll both do it at your best speed... AND, since you get something out of that too... additionally, you pick out my Halloween costume, anything you want... but you have to wear the corresponding female character costume... but you have to do it wearing nothing under the costume. Only the two of us would know."
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