And by long I am talking 16 years since I had anything resembling a friend or GF. 10 years ago I was finishing grad school and knew people but never did anything outside of class work.

I have tried simply talking to people, the only people that talk to me in person are bored cashiers that are way too young and just bored enough to enjoy watching me squirm.

I have tried looking for friends on dating sites and penpal sites. Nothing at all there. Can't get a response.

I even went outside the country and got a few people from China, Vietnam and Ukraine to chat a bit but I have no clue if they are legit and they obviously aren't hanging out with me even if they were sincere.

The two things that the people that will talk to me have in common is that they are women(which is fine-90% of the platonic friends in my life were women) and are roughly half my age: 25 +/- 2 years. Except one who lives in China and is 33, still significantly younger though. I just turned 50 and age gaps really bother me. My daughters are older than most of them but people closer to my age want nothing to do with me. I do look about mid-30's and probably act around that age.

None of those that talk to me are what I would consider serious options for friendship or more. Maybe I am too hung up on age but I am pretty sure my daughters would be upset if I started hanging out with people around their age or a bit younger. What could I have in common with a 25 year old anyway.

The reason I have been alone so long is complicated and a very long story. I got in bad relationships due to low self-esteem and some fairly serious mental issues. I figured it was the best I could do but eventually decided that if that was the best I could do it is not worth it. I still have those issues but am a lot older and I can handle my issues far better. I am not even medicated and have learned to internalize my issues so most can't tell. At my worst, I come off more quiet and withdrawn even though I have a maelstrom in my head. But you wouldn't be able to tell. Even during a psychotic issue my external response is hard to detect.

So I would like to connect now that I am in a better place and my kids have left and loneliness has crept in but apparently it is difficult to interact with anyone appropriate.

I am not sure if I presented my issue competently but any advice for developing personal skills will be greatly appreciated. If something isn't clear or you can think of a way to narrow this mess I will try to answer your questions. I know it is very broad and basically boils down to "How can I join the human race" but I guess that is the point I am at right now.

Thank you from reading this.

Edit: The specific question is in the title. Maybe that is too broad but that is where I am at. I listed things I have tried and specific obstacles. I am not sure how to make my issue less broad. It seems that if I had a specific issue with a specific person, I might find help? To have issues with a specific person I have to get past my problem in the title. I guess no one can help.

How about: If you met someone who had spent the past 16 years alone, how would you react and what could that person do to overcome any objections?

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    I would be seriously considering talking to a therapist if I were you. Social skills are not something people are born with - they can be taught and you can be desensitivized (be made used to) social interaction and new friendships. You deserve meaningful relationships, happiness and self-love. I seriously doubt people here can help you as this question is very broad. – Benjamin Gruenbaum Oct 26 '18 at 5:50
  • I understand it is a broad question, I can narrow it down to something more useful maybe. I have talked to therapists but they usually just twist me up and use it against me and tell me I should be alone for the rest of my life, which makes no sense. I am not mean at all and I thought that people should be able have at least 1 friend. The dating part is a pipe dream but who knows, maybe someday... – noone Oct 26 '18 at 7:06
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    A therapist is someone you pay to help and support you with your life. If you feel like a therapist is judgmental or not supportive or not on your side - get a different therapist :) – Benjamin Gruenbaum Oct 26 '18 at 13:52
  • Actually I don't pay them since I get free services from the VA but I have had many over the past 20 years and not one has been helpful, usually they just cause more damage so it isn't really a viable option. – noone Oct 26 '18 at 17:05
  • therapy has really changed in the last 10 years. I would consider seeking help again and giving it a shot - for example if you tried psychotherapy maybe try CBT or DBT. Then again you and me are different people and have a different experience - so it might just be me projecting. Hope you resolve this! – Benjamin Gruenbaum Oct 26 '18 at 18:42

You have no daughter at home, so you have time.

I believe the easiest path to get real friendship is to share something in common. I advise you to find a hobby, and most of all find a community about this hobby. Hang out with them, you will make friends soon enough if you share something together.

Also, it looks like the age gap is a problem for you, but I think you don't need to consider it as a problem. A friendship is a friendship, the age doesn't matter.

Last piece of advice: don't start to be paranoid. Of course not all friendships are sincere, I do not ask you to be blind. But if you start to be suspicious with everyone, it's basically cutting your own throat : you are going to shut yourself away.

I am in a "similar" situation : I am in another country (other side of the earth actually) for work. Outside of work, I do not know anybody. Obviously starting to feel lonely. And making friend when you barely talk the language is hard.

So I found a hobby, and gather with people from my country (over internet of course). Having friend to spend some time with, even if they are not physically here, is helping.

So if you do not wish to go out and meet in person at first (my case), you can find plenty of online community about your hobby. It can be on forums, Facebook groups, Discord...

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    I think you mean "not all friendships are sincere", right? – Erik Oct 26 '18 at 8:32

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