Dating Questions: How to just go and "have fun"?

Everyone says to just "Go and Have Fun" on dates.  

This is harder than it seems it should be, especially when you come from my zone.  I am sure after much longer at doing this I will figure out exactly what the "Go and Have Fun" means and exactly how to do that as each guy is different and their approach to dating varies.  I must say that the longer I have done it, it has gotten easier, and I am sure the longer I continue it, it will be a skill just like other things, that you learn to do better and perfect through experience.  However, since each person is different, it may always be a challenge.  

My goal is to make it as natural as possible.  To be able to just be comfortable being me.  To not listen to any of those old voices from others who have told me what is right and wrong about dating.  About how to show up in a relationship.  Exactly what to say.  How to dress.  What to do or not do.  I do my best to try to shut them off, boot them out, ignore them, but its hard when you wish you could just delete them and remove them from ever having been in your head in the first place because the foundation as to why they were "right" wasn't a foundation built on faith and trust but one of fear.  I know being able to just be myself is going to be the biggest key to my success at this because anything else doesn't feel right.  Yet, it is still one of the hardest things I have ever done and allowing myself to be just me, relaxed, in my true personality, enjoying the moment, sometimes is just beyond difficult.  And other times, it isn't at all.  

You might be saying why?

Well, it feels like if I honestly just make my purpose to "just enjoy the date" with you then I am not finding out the things I should be about you because the dating process is supposed to be an evaluation and learning process.  I don't want to continue going on dates if you are not a person who has character, appropriate boundaries and like minded interests with me.  Asking questions is the only way I learn those things.  Right?  But then if I try to find out information about you, I feel I turn it into something where I am actually interviewing you and taking mental notes and it is so much harder to make and keep fun in the mix somehow in this process!  Some of the dates I have been on I have actually been able to accomplish both, and these are the ones that are truly the best!!!  

Then when you are able to achieve both with someone, then you have to play "the wait and see game".  It's not like I have this mission to find this man in 2014 and get married, but at the same time, just letting life happen, trying to act like you don't care and not show that it matters to you if you ever hear from them again or if you will get to see them again, that you are just cool with whatever happens is kinda hard, really hard when you want to spend time together.  I am not doing this for kicks to see how many dates I can go on to find a man that wants a relationship.  Promise!

I get frustrated when people say, don't rush into anything.  After waiting 37 years, I promise you, I am.not.rushing.into.anything.at.all.  I promise you, I want the guy that is the imperfect Mr. Right who is the perfect match for me.  I want the best.  The absolute best and I will not settle.  I have no need to settle.  I have an awesome life single and the only reason I want someone else is to take my life to another level that is more awesome than what I currently have and if its not that, its not worth it.  I will find him or I will remain single.  I know I am worth it and I know he is too!  And I want to be the perfect match for him too.  I want to blow him away.  I want to be awesome on such a level that he can't live without me.  If he doesn't feel I will make his life better, why would I want him to want me?

Dang.  It's very tough to be dating.  Trying to figure out this.  Who made this so complicated anyways?  Should dating be this complicated?  

Some days I think staying single would be a better option.  I can control my world this way and believe me its not a shabby world!  I have God and really do I need anything else?  Part of me says no and part of me says yes.  That's where the conflict lies.

Oh dear God, please help me through this to know what you want for my life and help me to figure out what I want too!  You know what is the best for me.  You know what I need.  You know what I need.  You know who, if anyone, would be best to be that person in my life.  I pray you give me answers.

How did you make the dating scene a bunch of fun?  What to you makes this process more fun?  Less complicated?  Easy?