Attached Link: Feeling lonely? Rent a friend

Not free but apparently a growing trend and perhaps a way to get practice meeting and talking to people.

I agree about giving the older ladies a shot. I'd still be hitting on older women, but older now means they have to back at the nursing home by 10.

Most churches, synagogues and mosques probably have singles groups, that might be an excellent opportunity. I think one key point is to not panic if the conversation seems to flag. Pick up on what the other person is saying, look for hints of other topics they might be interested in to keep things rolling. Put up that great Poser movie you're making on YouTube and then sit in an internet cafe watching it. Someone my comment and then when you said you made it, a great conversation starter.

I don't entirely disagree with Wolf's observation - the internet can in fact lead to greater social isolation. OTOH, they're certainly various support groups on the 'net specifically geared to helping people overcome shyness, though they're no substitute for meeting people in the real world. Shyness in an of it self isn't a problem. It becomes a problem when it causes you distress or interferes with your life which seems to be the case for you.

"Democracy is a pathetic belief in the collective wisdom of individual ignorance." - H. L. Mencken