Matt, I've been to Thailand a few times, and I love it there. I think you will be just fine!
If you get a chance, check out the area around Phuket. If you stay on the Island of Phuket, stay on the Western side, it's much nicer, but try and stay outside of the town. I found that it was cheaper to stay in a nice, beachfront resort and rent a jeep than it was to stay in town, and one heck of a lot better! The tourist towns are things I avoid like the plague, and if you don't get out of them you might not like Thailand very much.
If you have a 4X4, you can safely drive over the bridge to the mainland, and explore places like Phang-na bay, and down the coast to Krabai, two of the most unique and spectacular places on the planet.
One last word of advice: don't take the Phuket-based tourist excusrsions to Phang-na bay. They cost plenty, and heard you around in a group like cattle. Instead, follow the crude hand-panted signs that show the shape of "James bond island" once you cross the bridge from Phuket to the mainland. They will lead you to a small dock where they have charter-guides. So, instead of going in a tourist cattle-boat, you get your own boat and guide, and it costs about 1/5 what the tourists pay. Also, you get to plan your itinerary from a photo book (don't miss the sea cave).
The guides can be a bit disconcerting, as they are Moro tribesmen in traditional garb, including their huge machete, but I never had trouble with them, nor did I hear of any.
But above all, HAVE FUN!
Ummm, but not too much fun! Thailand is the AIDS capitol of the world and has a booming sex industry, and both the male and female hookers can be very cunning in their "pick ups". Beware, but if perchance you do decide to play, at least be safe.