#30: Stay Classy, Florida
This next picture comes without a caption, which isn’t needed because the picture itself really says a lot. I wish it surprised me that you could find this tackiness in Florida, but it doesn’t. Although to be fair, there are probably other states that would find this equally amusing.

I mean, I guess we ought to give this guy props for trying to make sure he doesn’t get himself in any sticky legal and moral situations with underage girls, right? It’s kind of a low bar, but I guess it’s something. At least the girl in the picture seems to be impressed with him.