I have used this successfully in cities where I have an hour or so to kill.
In Pittsburgh one spring morning, just like today, I wandered around downtown asking for directions to the main railway station. I had a delightful time, met a dozen or so nice Pittsburgians, some of whom insisted that they walk me to the station. Of course, from there I asked a different stranger for directions back to the restaurant.
(2) Twice a day, walking along the sidewalk, say "Good Morning!" to a stranger coming towards you in the opposite direction. (ii)
(3) In the Food Court, or as you are greeted into the diner/restaurant, you will be asked by the waitress or cashier "How are you today". Just for once, don't respond "Good, Thanks". Instead say "Hungry and Thirsty", but smile and look them squarely in the eye as you say it. (iii)
(4) In the supermarket, or when paying for the gasoline you have just pumped, or at the ticket wicket, greet the cashier with "Hello". No more, no less. At the end of the transaction, say "Thank You". (iv)
So now you think I'm going to tell you that these four exercises will cure you of your shyness.
Wrong. Utterly Wrong.
I am one of the shyest people you will ever meet, but by practicing these and other mini-dramas I come across as confident, just long enough to start a conversation.
If you've ever met me at a networking meeting, you'll know that what I say is true.
Thanks to Li Yin for the Inspiration of this Post.
(i) You know that I know that you know how to get to work and how to get home. The other person DOESN'T know! All you need to do is ask a complete stranger "Excuse me, is this the way to the northbound trains?", or "Does this train stop near Queen Street".
(ii) It doesn't matter whether they respond. And you just keep walking. You're not trying to pick up a date. You are walking, and saying "Good Morning", no more, no less.
(iii) Once you get used to the warmth that comes from this exchange, you can go for the Black belt: "Hungry, Thirsty, Tired, Cold, Broke, Underpaid and Overworked".
(iv) It is of vital importance that you look the cashier squarely in the eye while you issue these greetings. The cashier is a human, not a machine.