Trying to explain something to a coworker who's younger and originally from Pennsylvania:
He's got a shirt. A shirt a friend of his had made. He thinks the shirt is way awesome. And I understand his reasoning for thinking the shirt is awesome. It has a pop culture reference in conjunction with a presidential candidate, all to indicate the coolness of the candidate.
Here's the thing. Unbeknownst to him or his friend who made it, there's also a stereotype associated with the representation on the shirt. And he's astounded, because he's never heard of it. On one hand, yay! On the other hand, this is the south where we *are* aware of the stereotype and I think he'll end up getting some grief should he wear the shirt. It's hard to explain to the young that just because you don't mean it the way it comes across, that doesn't mean it still won't get you in trouble. Just because you don't know doesn't mean other people will look at you and automatically know that you don't know.
The shirt says "Obama 08", has a picture of the Kool-Aid man and then says "Oh yeeaaaaah" underneath.
(The amusing part was explaining the issue to him and the other person from Pennsylvania. We have three employees from PA who are 28 or younger, and they'd never heard of the Kool-Aid stereotype. They had heard of the fried chicken stereotype. Then we had to explain about watermelon. I think by the time we were through, they were pretty darn confused and couldn't figure out what the hell was up with food stereotypes.)
Bless his heart, he's going to get schooled somehow and I feel bad for him. But he's been forewarned. At this point, he's operating on youthful optimism. Unfortunately, the reality is that, for his best intentions, it's a lesson he has to learn for himself if he won't listen to the older and wiser that know it's just not going to be cool like he thinks it's cool. He has "faith in people". He doesn't realize that people don't know him from Adam and can't see intentions, while they can see the shirt.
I did tell him flat out, though, that if he's out anywhere and sees someone with a Confederate flag on their truck or vehicle? Avoid them like the plague. Because being anywhere near a flag with that shirt would really get him in trouble.