Although I know our parent’s issues can influence our self esteem, it doesn't seem to be the root cause of this particular feeling of worthlessness as stated in your original post.
By the way, I like the great way you handled those attractions to the man by bringing them out into the light of day and not letting yourself be caught up in some fantasy crush or painful affair. Good job. Stay free.
A lot of what you were basing your worthless feeling on in your original post seemed to be more about the financial aspects of your childhood and your present situation or position compared to someone else's (the man and his family). You felt worthless and undesirable because he is from a well-off family and you are not.
The feelings are real and painful and you are courageous to examine them and their power over you. You already know this but I just want to add another voice to yours and say that the process and data used that led to those feelings is all based on a lie. There is no such thing as a worthless person.
We are all sent here from God, our father, who is pretty well-off himself and our worth has been determined and set by Him. Nothing of the world can change our value, neither add to it nor take away from what we are made of, which is God.
We may have the use of different things and be able to gather up more stuff around us and get pieces of paper with our names on them, like diplomas and birth certificates, car titles and deeds, but we are all still going back to the same place, to God, and all that will be left here to rot.
Whether we have a lot of stuff or a little, we all have access to the true riches and we all have the privilege to use our stuff to make life easier for someone else. We all have the opportunity to take what we have been given and add to it and we can all be proud of how well we have accomplished this whether we started with a little stuff or a lot.
That someone back down the line in that man's family, was able to increase what he had been given at a faster rate than those of your family, whether due to the luck of circumstances or due to initiative and wisdom, that does not make you worth less or anyone else worth more.
Wealth is not evil and poverty is not good. But there are also "poor little rich kids" as well as "rich little poor kids". And "rich little rich kids" and "poor little poor kids", the first adjective being a matter of choice and character but the last being more a matter of the circumstances of this world.
My cousin, when struggling with her own insecurity and wealth issues, came to the conclusion that we all came from "white trash". We both came from the same grandparents so I felt sorry for her. Must have been her daddy that was "white trash" because my grandma and mother and aunts and uncles were all diamonds with vaults full of wisdom and kindness and generosity, the true riches and that was my inheritance. She disinherited herself from all that, I guess. Or just wanted more than that.
If your parents and grandparents were poor in all those things as well as in money, you seem to have started your own vaults of both kinds, for your children and grandchildren. Your comparison of yourself to someone else's success can be a good thing if it gives you hope that it can be done but don't allow their success to make you feel worthless or hopeless.
Because of family obligations and circumstances, our aunt Della hardly ever had two nickels to rub together and yet she made the very best of this life she had been given. She never forgot that she was the child of the King of the Universe and she never treated anyone else as less than the same, no matter which street they lived on or which color skin God gave them and no matter their preferences, choices or mistakes. Through her efforts to continually improve and educate herself, she became like the Buddha or sage on the mountain for our family. Everyone left her presence feeling like they were special, not because of what she said, but because of the importance she placed on hearing what they had to say.
If I was ever going to allow myself to feel worthless in comparison to another, it would be someone like her. But instead her success and they way she multiplied what she had been given, just the breath in her lungs and the blood in her brain and the ears on her head into eternal, never-ending riches, this gives me hope that I can do the same.
You can have less stuff or more stuff, along with the distractions and responsibility of that stuff, it's your choice. But you will always be golden
and loved and part of your work here on earth can be to let everyone else know they are too, if you choose to accept the mission.