"From this experience it seems best to be honest with myself. And being honest doesn't mean being bad, selfish or ungrateful; although it does mean not being able to please others every time."

^Love this.

20 year olds still go to [I]raves[/I]?!
I thought I was back in the late 80's/early 90's for a minute!
Do they still play loads of Prodigy and Portishead and take loads of E?

Hey I can relate. It's hard though. Today is my dy off work and I promised myself I would do a list of things. I know they would have made me feel better if I would have done them too but doesn't look like it's going to go that way. I read somewhere that the best way out of this is just to do something but isn't at exactly what the problem is lol. Hope things went well with your boss xx

Keep at it man. Keep on that treadmill because eventually you will be where you want to be. The world becomes a better place when you bring your best version of yourself to it.

It depends if you rely on pop culture as a source of conversations. I know many people who openly reject pop culture and aren't embarrassed to not know latest films, pop stars etc. but they have no problem continuing to be sociable.

I had a similarly isolated childhood to you, and it took many many years of hard work to shake the feeling of being different/worse than everyone else. I learnt to be gently curious about the things people are passionate about. Not saying you absolutely should do this but it's one option to try.

So for example if someone talks about a film you've never heard of, investigate: ask them what the story is, when they first saw it and how did they react? etc. I guess you have to be genuinely a bit curious about it before asking questions, because it probably comes across as disingenuous if you fake it.

You will feel more connected to what it was that made this piece of culture so memorable, even if afterwards you decide you're still not iinterested in it, plus you'll have had an enlightening conversation and perhaps bonded a little with another human being.

You're not alone, got a friend who is exactly the same, even as far as despises popular. Also guy on panel show Ian hislop famous for no knowledge of popular culture.