Is anyone introverted by nature but wishes they were extroverted

I'm naturally introverted, too. I have no problem speaking up when I feel something needs to be said, but I'm uncomfortable with small talk, etc. I don't really "wish" I were extroverted, though. I'm pretty happy with myself. I don't think the problem is the fact that you are introverted; I think it is that you are a little lonely--and you think this is because of your introversion.

Rather than trying to talk to just "anyone", I think you'd be happier if you found just a few people you could really talk to about what you think are important issues and interesting ideas.

If you really think the problem is your introversion, you can always treat it like a phobia. Whenever a psychologist treats a phobia, they introduce the irrational fear little by little to the patient--to let the patient see that nothing horrific will happen when they are exposed to it. In your case, that would mean, you should make it your goal for the whole day to talk to just one person you do not know. For example, if you are in a line with people waiting, just say something like, "I found these kit kat bars --2 for $1" (Obviously, I'm no good at this either.. haha) Anyway, you get the idea. My brother overcame his introversion this way and is now completely fine having "small talk" with strangers.

Oh and "cleopatra" 's idea about asking other's questions has always worked for me. It takes the pressure off--and most people love talking about themselves--and they think you care.