I have no social skills, am incredibly boring, and want to end it

[Janis N.]

This will be tl;dr.

I used to be very shy until I switched schools at age 16 and decided to "reinvent" myself (I had read some self-help books, etc.).

I made it a point to talk to many people/chicks/etc. and I gradually got better at it.

That carried on for a while until I realized I had been pretending and I don't really care about most of the topics discussed and don't care much for most of these people.

Now I'm again not a very talkative guy about most the topics the other people discuss... I don't own a TV set (waste of time). I don't follow current events that much (again I just don't care). I don't have anybody to talk deep spiritual/emo stuff with as I think a lot of those things are fairly clear or clearly unclear so there isn't much point in discussing that.

I have a few close friends with whom I really like talking, but making new ones is a problem as most people just don't impress myself enough for me to try to leave my best impression on them.

Not sure how that helps the OP though... perhaps basically my point is that if you practice you will at least be able to pretend to be sociable. Just practice enough. I used to make a point to start a conversation with every neighbor on the plane or any new friend my friends would have, and so forth. It sort of worked (yes we had conversations, people though I was funny/sociable/etc.) and sort of didn't (as now I no longer do this).