It's all machine spinning if you let it. It's your life, man. Part of it maybe comes down to the fact that this is all rehearsed - we look at ourselves, we analyse, we break it down, we think about the girl, we think about what we're going to do, in some manner or another, and we make it work, or we try our damn hardest. For some of us, we've run each and every scenario out in our heads so many times that our own reality seems like a second life.
We take these Women into our worlds, some of us are not even comfortable in our own Worlds to begin with, so taking somebody else in is going to be like this big fascade of rituals and regulation, which is maybe part of the problem for a lot of guys. It's fake. Much like confidence you can't 'fake it', you can build it up, and you can put on a show, but once you make the smallest mistake it's going to be clear just how confident you really are or aren't in many cases.
If that isn't the problem, and you're truly comfortable in your own 'world', then you make the rules, you set the standard, and if it's not up to scratch then you raise the bar. You make yourself even better.
I get how it can be though, even if you are an interesting person who knows a lot of people, you can't exactly be that guy all the time, you can't be around the exact right people at the right time all of the time, but you can certainly raise the bar in terms of where you go, what you do, how you run the show. Don't make it awkward if you don't want it to be awkward.
And maybe if you're not enjoying the companionship of the women you're seeing, you're maybe seeing the wrong ones. When you get into this whole thing, some people seem to think you just have to go after 'hot' women, unattainable types or otherwise. Women your friends think are attractive. No. You can still go out there and find women you're actually inspired by. You don't have to make this an ego dripping session. It's all on you. Slow it down.