Just be what you like being even when its in solitude, it should not have to be a negative and you should not consider it to be a negative because accepted social norms that do not count for you.

Come at peace with what you are and stop focussing on what you cannot do but try to seek other things that makes you grow as a person and ultimately brings you happiness.

There is no real advice on here. People wrongly assume that everyone has the same opportunities in life and are equal. Anecdotal stories do not change anything. Just be yourself advice is useless because that only works for people that have no problems. I tried therapy and medication and both made no difference in my life and I gave that up. I started and not completed multiple college courses and jobs not fitting within a month and quitting out and spent long periods of unemployment and dependent upon welfare and family support. Multiple jobs I have had I quit them all or was fired within a week, I just did not show up or simply walked out. I have not bothered with social media or online dating because there is too much effort writing profiles, sending messages for no responses and I just can not be bothered with wasting time. Luck plays a huge role in determining success in life, some of us are born with good luck and some of us are born with bad luck. 

Depression. Anxiety.

I messed up so many chances with sweet and nice women because I think with my penis.
I‘m actually starting to feel bad about that.

If you really want good advice and help, and if you really want to change your situation, you should go see a psychologist or something like that. They can do a lot more to help you than any of us can.

A grumpy middle aged man like me approaching 40, is too stuck in my ways and unlikely to change. I have accepted the reality of my life and drink lots of wine and ponder what may have happened if life was better from the start. I hated being unpopular at school and spending hours upon hours playing video games. I envied the popular kids because I always wanted to be popular. Being popular usually guarantees future success in life. I have found it hard to recover from being the sad, unpopular kid. It is like a dark cloud that never goes away

You know that most those "popular" kids are now working the worst jobs. This is mainly because their ego outweighed reality of adult life and they thought everything would just be handed to them.

for those interested, In Japan you can rent a girlfriend, boyfriend, a friend or an entire family. contracts can last up to 3 years. the most intimacy you'd get is a hug.

If I can't get a blowjob from my entire family, I'm not interested.

Well yeah it indeed most likely never goes away but doesnt it get better to handle as you get older?

I am not sure you have really accepted the reality of your life because you ponder so much about missed chances in the past and how they affect you now, it is not wrong to ponder about them but you seem a bit consumed by it.