I’d like to share a short story with you , it may not help – as all issues in life are relative but I hope you will get something from it.

I had traveled the world , come from a fairly affluent family had many friends etc but eventually I squandered a lot of great opportunities and my addictions led me to run straight into many failures. These failures sort of “culminated” in my getting arrested for possession of prescription pills in Atlanta and spending six months in Fulton County Jail , not even calling any family and not really having anyone actively looking for me.

Understand that I had great expectations from life andfor a time could sustain this fiction with a thin coating of material success. But here I was . Broke , in an extremely rough prison and without a person in the world who I felt I could call. But you know , in a strange way I felt free for the first time in my life.

After that I got a job at Michaels (a retail craft store) as a salesperson and went from six figures to $7.50 an hour. I put my soul into that work (even though I could easily have hated it). And thats the key, that’s how we win no matter what by making joy our strength.

I am not back where I was financially, currently working as an electricians apprentice and at the age of 32 living with my Mom. A complete loser, right? Sure , anyone can categorize me that way and they would be correct , only I don’t feel that way at all. So in my internal world which is the only one that matter I am happier and more successful than I have ever been.

Why? Instead of “living with my mom” being some horrible mark of shame I see it as a great opportunity to enjoy and improve a relationship with the only family I have , I was, honestly, terribly lonely out in the world with all the trapping of a “good life”. Instead of starting a new, much lower paying and less “prestigous” (its funny too me that I ever had such a simple understanding of life where I thought my job defined me) position feeling like a drop to the bottom, its an exciting new adventure where I get to learn so much about myself and now my new dream is to start my own business selling solar panels and to that end I have saved $50,000 .

I am not saying that anyone should follow my turbulent trajectory or that you need to fail at anything only illustrating that a change in perspective is a choice and an extremely powerful one. I can say , for sure , that these last years have been the best of my life and I am growing as a person in a way that I never would have in my old life.

So I approach every day with humility and gratitude. Our stories are different but I would suggest you trick yourself into loving your job and your life while you plan for the future. No time on this earth is less valuable than any other so while you are making these plans for the future, you can get a lot out of what you are doing right now.

I know how hard it can be and I wish you the strength to hang in there but don’t forget how amazingly exciting the journey ahead of you is going to be and that without a doubt, in your future you will miss certain aspects of what you are experiencing now.

Best of luck!

Hey Spidey!Disclaimer: I wrote this whole reply before reading your last update but am still going to post it because I think some of it may be helpful. Btw I think you are pretty much handling the situation perfectly. We can always armchair quarterback and try to analyze where things could have been done differently, that is the luxury of hindsight but you are on the right path and no man makes it through this life without mistakes, rejection and learning the hard way when it comes to dating. The good news is that is where the learning gets done, just don’t over think it , you have learned what you needed to up to this point just keep operating outside of your comfort zone and you literally cannot fill

There is an irony to these situations , which in a way is connected to the ironies of “mindfullness” and happiness in general. As has been mentioned, the very act of over-thinking these situations sort of puts you in a disadvantage from the start. I don’t know if this is practical advice but I’ll share at the risk of writing useless or even counter-productive “advice”

I think you should focus inwards. Focus on your strength , find your joys and (flaky as it sounds) situations like this will sort of become “details”. Not in the sense that they are not important but because they will fall into place naturally and simply. Now do not become overly frustrated or take any of the associated negative feelings to heart. The truth of the matter is that any guy , at some point in their life is bound to be rejected , maybe multiple times until we sort of lose the fear of rejection and become comfortable with our bodies and minds. Once that happens the seduction is just automatic , until then it is awkward but that awkward is all part of growing. The very act of taking the risk of rejection is a very courageous move and honestly, no matter what you will be better for it , that I can promise you.

Women are extremely intuitive and very socially aware (much more so than most guys–myself very much included) so they are going to be onto the “you” which we try very hard to hide from the jump ;). But this is a great thing because it means by changing the inner life we will have a revolutionary effect on how we are perceived. In a way I do think you can “fake it until you make it” but there are very definite limitations on how far you can go with it and its probably less painful to work with what you have.

Some people are able to have that vibe early on. I wasn’t one of those people and never thought I would be. You seem to have a lot going for you so if I could, eventually approach these situations with calm and confidence , please believe me when I say you can or will be able to, if not now , then it is only a matter of time and continuing to take risks in order to expand your vault of experiences.

I’m sorry that there is no simple answers but you have a lot to look forward and ANYTHING you do (within reason) is the right thing to do because as long as you are putting yourself out there you will get results either tomorrow or in the near future.

Good luck!