Hook up with a club. The HAM guys LOVE to talk and assist if you have questions or need help setting something up. There is a wealth of information out there (along with a wealth of opinions).
If you want to "rag chew" it helps to get known by those in these communities. Also, like shooting ranges, each club has a certain flavor or charter, it may take a while to find one the fits your interests.
It is really amazing the diversity of activities in the amateur radio community from emergency communication, to contesting, to experimentation, to military auxillary (MARS), to weather watching, to digital packet radio, to speaking with the space station/listening to satellites, on and on... Various clubs tend to focus on certain areas.
As
s&w3913 notes, "Also it's sort of like trying to approach the group of people talking at the local diner, mcdonald's or dunkin' donuts who don't know you." So, they may not answer you on the repeaters even though they are listening (unless it's an emergency or something). Don't get discouraged.
Plus, having call signs memorized is a trick in itself...