Firstly, it is better to get a regular connection if possible. You will get better deals, better weed (probably), and you will know for sure that you can trust the person. Not everywhere has places you can just go and expect to be able to find somebody who deals. You will have to find a specific dealer and get in touch with them every time you want to buy. Asking on the Internet for hook-ups isn't a very good idea either, considering how many scammers there are when it comes to buying pot and the Internet (plus, you never know who's a cop). Asking around on the streets of a big city is risky, like you said, and I know from experience that it is frustrating and awkward but it can yield good results if you're lucky.

Unfortunately, you probably won't be able to find a connection if you stay a "closet smoker". You usually have to hang around with other smokers before you find a connection (and believe me, you are not the only older smoker; there are a LOT more of them than everybody thinks!). Just remember that no matter where in this country you live, there are plenty of people around who smoke pot and people who sell it to them, and there are people who would be happy to sell to you if they know they can trust you. It is just a matter of infiltrating that "crowd" and once you find out who all the dealers are, choosing somebody nearby who will reliably give you good pot for a good price. It isn't as hard as it sounds.