Seeing that I turn 30 next year and never had a legit relationship my entire life, when would it make sense to question whether I will ever find a wife and have a family of my own? I am at the average age where my peers are getting married.
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In other words, when would you say, "if it hasn't happened yet, there is a good chance it never will."
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You're a guy it can happen for you at any age. If you are 30 you can date 22 year olds. If you are 40 you can date 28 year old's if you are 50 you can date and still have kids with a 33 year old. Just go find the right person and don't worry about it.
There is no such date or age. Some people find their SO early, others late. It's life.
Work on yourself and hone the skills, knowledge, and qualities you find important.
You have to question what you are doing wrong, or maybe you are simply not doing enough.
What avenues are left? I work from home. I go to church. I have a brotherhood of single friends. Online dating has never worked out. I am no longer in school. There are not very many places to meet women organically and conventionally, unless I want to go to bars, but even there I have been taken advantage of and scammed.
Also, I am shy and socially awkward. I have a good job and make good coin, but I am just starting to get my life back together.