I think he meant to say "If I had a dollar for every woman who asked to take a selfie with me and who slipped an arm around me and let it drift down below the beltline, I'd have a wooden nickel.
“If I had a dollar for every woman who asked to take a selfie with me and who slipped an arm around me and let it drift down below the beltline, I’d have at least a hundred dollars.”
He’s 6’4” so it’s likely to happen by accident.