I think that's what a lot of people are looking for. Although you might luck out and find someone in your own age group to talk to, chances are that pretty nearly everyone you know is as afraid to open up to you as you are to open up to them (and as likely to step on your toes a bunch of times as you are to step on theirs). You'll probably need to proceed cautiously both with picking the right person and with sounding them out.

Therapists and counselors are trained to be good listeners (among other things), so that really may be the best place for you to start. After you've had some practice talking about emotionally-charged subjects with a professional, I'd expect you to be better able to approach friends in your own age group, to spot those that are ready for a serious conversation and those that aren't, to tell where the conversation is and isn't going, and to guide it in directions that'll work for both of you.

You could also get some practice here at PC if you wanted to. It's a little different from IRL, or offline, or whatever you want to call it, but we do have a lot of great people here.

Good luck, Morgan!