I was painfully shy up through college. Now I’m not. I have lots of explanations, but nothing unmistakably correct.
One of my favorites is the Eastern/Jungian “swiss army knife” description of human personalities. Suppose that all human beings have “multiple personality disorder,” but the fragments are held together by a strong misconception of being a single “I.” If you try to do things to weaken your self-image rather than strengthen it (pursue egoless states rather than stoking your self-importance), then the separate personality fragments can more easily act as independent tools when required. You can be seized by an architype when circumstances require it.
I look back on my own history and see that I was not a “shy person,” since I wasn’t shy when working on projects, or while reading, exploring outdoors, singing while alone, writing, sleeping, etc. I had a variety of personalities. Storytellers. Intense focused artists. Life-of party types and intellectuals. Yet I was always dominated by a “shy person” personality during actual parties, etc., and all of the other versions of myself were out of the picture and forgotten. Something always pulled that “shy” tool out of the swiss army knife. Something about self defense, but it’s not clear.
How did I get over this? I can’t put my finger on it, but it happened after years of brutally truthful introspection, of forcing myself to go to useless parties, of forcing myself into public speaking situations, etc. I gave up the idea that popular people were a**holes, and stopped swearing to never become one of them. I totally accepted being a loner type, and gave up all hope that I’d ever meet friends/lovers at parties. Very freeing, no more concealed neediness and dashed hopes. Sometimes I would screw with partygoers’ minds. Sometimes events were even fun.
I started being outwardly honest, freely admitting that I was a nerdy wimp who reads way too much and has no girlfriend or any hope of getting one; no longer trying to desperately maintain false facades to keep people from finding out. I also gave up the idea that I was superior. No longer “special” or unique, and I started assuming that everyone in large groups of people was exactly like me, like cells in an organism (although some of them could bring out better tools.) Also I developed an expanding array of “pet topics” which I could hold forth on for hours once someone got me started.
Of all these, which was the cure? Can’t tell. But I suspect it was the part about not lying to myself anymore; of confronting uncomfortable ideas and shredding illusions that I’d long been trying to shore up.
In hindsight I think my “shyness” might also be labeled “depression,” and in slowly defeating it I was somehow changing brain-chemistry to where I wasn’t trapped in one narrow “I” or personality, but occasionally had access to a whole array of them, plus the large creativity hidden between them, and I migrated away from “depressed” and towards the “manic” end of the spectrum just enough to be normal.
More recently I spent stunnigly huge amounts of time for several years hanging out on newsgroups, getting into longwinded discussions, even sparring with nasty flamer types. This definitely had an effect.
Have you ever considered using, um., artificial aids? If a stranger comes up and starts talking to me, I can reach into my coat pocket and grab… rare earth supermagnets. Tiny exlosive pellets. A quarter which was compressed to half normal size by a titanic magnetic field. LED mini-light that lets you see the capillary bed inside your eyeball. Two laser pointers for simulating some orbital mechanics or a game of “Pong” on the ceiling. A fifty power microscope to explore civilizations growing under fingernails. Etc. Etc. It all started off as stuff I messed with when alone and bored. But eventually I was saying to strangers: “Hey, wanna see something REALLY COOL?”