Having trouble finding friends

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I have the most trouble finding friends. I have to go and do things by myself and it is very depressing. I have had this issue for years. I always find myself on the same wavelength with people much younger than me sometimes teenagers and I am almost 40. I don't know how to even start talking to anyone. I am scared to even say hi to anyone especially if they are female. I always get the sense they would never give me the time of day. I have had trouble with this for 10 years. I feel I have nothing in common with any female my age or even close to it. I still live at home and have never been married and no kids. I have more in common with a high school graduate, but being friends with anyone that age would look creepy. Need some help. Tired of sitting at home all the time alone.

Not sure I can help, but I can relate.
I underestimated the process of gaining friends, it was a simple matter of getting introduced to them at school and talking to them, which meant you essentially joined their group and had access to more people.

Without the 'automation' of school I don't even know where to start... I'm fairly fine with conversations, I can hold one and engage fairly well. My main problem is that I feel too awkward to start one. Messaging a friend, let alone a stranger, feels strange and awkward enough "do I just say 'what's up?' or something?"
That's also made the friends I had from school become distant; it's not good for a friendship to never start conversations, but simply reply to them. Replying isn't enough, sometimes you have to start it first. Yet I just can't.

Then there's another dilemma, actually becoming 'acquaintances' with someone. It's no longer as simple as 'we're both in a group at the same time every day for school', now to talk to someone again I'd have to get their details/facebook/something like that. Yet, after a conversation, it never feels right to ask something like "want to talk again on facebook or something?"


On another note, I also feel like I'm more on the level of younger people... I'm technically an adult, yet I really don't feel it... I know I've always been more mature then most in a lot of ways, yet in others I think I'll eternally be childish. I think it's the AS, that only parts of be 'grew up'...

Well everyone is different and if you think about it and maybe brainstorm a bit you should find something you have an in common with some women of your age. Even if it is not something most people have an interest in.

You can always try meetup groups or search online for people with similar interests. Facebook is another great place to find people you have in common with. Check out what pages and groups there are, and search 'people who like....' then use the filters to see who might be living locally.