You sound a lot like me ( except you are about 2X better off than I was at that age). With regular people, you let your guard down and just go for it. That could be the difference. As soon as you "try" with women, they can usually pick up the insecurity very easily. Thats why my best success was when they had to enter my sphere of influence and not the other way around. This is why so many guys on this forum advocate dating multiple women before actually getting in a relationship. I won't go into the merits here since they are plastered all over, but the idea simply being that you can't really focus too much on her.
I'll be honest, at first I was a fake it till I made it type person. I remember going up to girls when I was in my early 20s and trying to talk to them only to get shot down. After reading "The Game" I learned how to approach a little without being desperate looking. Confidence is a weird thing. In many ways, actions begat confidence even if your actions aren't confident initially. For example, when you approach a stranger and are able to have a funny conversation ( despite being nervous as hell), your brain seems to subconsciously believing you CAN approach again. This makes the next approach better, and so on. Eventually its a fun game. However confidence works the other way too, when you start feeling like crap, you don't feel like you can approach, which makes each approach worse.
here is what i used to do when I killed it. First, believe that you are the ****** and that people want to be around you. Obviously you have friends, a good job and all of that so its actually true. Cool. Next, when you are out, if you see someone you want to talk to...3 seconds...you just do it. I stopped approaching directly, and instead made it look like I was passing by - open with some question or a quick observation. Observe body language, and see if she responds. If not, just keep going and no harm. If she opens up, keep asking questions. Eventually you won't even have to try. Do what works well for you. Back when I was your age, I tried this in Serbia where no one at the bar spoke english. I even ended up with a phone number, although asking for that was difficult because of the language barrier. It goes to show that ones actions are more important than what you even say!
If I had to summarize, it would be this. Enjoy your situation in life. Enjoy the fact you *have* friends and can afford the opportunity to be out and among younger women. Walk into the room with a yuge smile and just socialize. One day, the friends will grow old, get married, have kids and it will be over so live in the moment. Take it from a guy who is now at that stage and fondly misses those days of going for it.
Good luck buddy.
