Any of you folks in your 30's and 40's have any advice on how to fast track this process a bit?
Also talk to people. Talk to them all the time. Standing in line at the store. Passing by on the street. Just make an observation about something to start the conversation. Compliment someone. Over time you'll get two things from this. First, you'll realize that everyone is just a person like you (like, the subconscious part of your brain will get the message). Second, you'll get a bunch of little rejections (weird looks, things like that) over time in a scenario where you basically have no skin in the game. You'll no longer care about rejection and you'll realize that people rejecting you almost never has to do with you - it has to do with them.
I'm 33, haven't cared in a long time. Just do stupid shit and own it, with time, it is still stupid shit, but you won't feel embarrassed by it (I live in a posh area, my kid goes to a posh school, I wear 15 year old tshirts (that lost all their color due to washing), no shoes/socks, use shorts 90+% of the time)
edit: And interestingly enough, even though I'm married and with little interest in that, the amount of female attention I get over the ones that care is amazing (and no, I'm not good looking, 5'6, bald earlier in life, long beard and a few scars in my face)
For me it's in some ways similar to the part in the debugging or performance tuning cycle where you're just watching things happen, letting logs and metrics scroll by on your screen. Externally, you look like you're not really doing anything. But what you're doing is noticing relationships, reoccurances, rhythms. At some point you say, "That's odd. When X happens, Y follows. I wonder why that is?" And that's where the magic begins.