Yeah Charleston is dorky to "outsiders". Preppy almost. But to those of us down here who know it, it has a very cool underbelly.
There is no club or restaurant in Charleston you couldn't walk in the front door and be served well, but I dare say there's a dozen or so I could walk you in the back door and you'd be better served. Being Greek and a foodie I'm sure you know how this happens.
I spent a bit of time in Charleston and I remember most of my time there as utter boredom. Then, I started dating a girl going to the College of Charleston (although I never once saw her attend class or open a book) and suddenly it was like living in an entirely different city. That was a few years ago, back when ecstasy was the cool thing to do. I used to go with her and her friends to weird "private" clubs. I don't think any of them were truly private in the sense that you had to have some sort of membership or secret password to get in, it was just that if you didn't know that they existed you would never be able to find them. The entrances were always in the back through an alley or up a fire escape or just a plain metal security door in between a couple of dumpsters that was completely indescript. The weekend before I left, the last club she took me to was the wildest and even though it looked like a small cheesy 1970's disco it was a great time. I think it was named something like "Circus" or "Carnival".
Anyway, thank God I got to see that part of the city, and ever since then, as I have moved on from town to town, I always wonder what secret underbelly I'm missing out on.