Design Research: How do you get strangers to talk to you?

Before I begin, know this.  I can be moody.

This is just something I know about myself.  In the early morning, I have to work at speaking.  It's as though, each morning, I'm going through a process of accepting that I inhabit a body all over again.  So, until about ten o'clock it's just pain and grumpiness...really.  Even if I'm smiling at you.  If it is 8am there is a high chance I am uncomfortable with the fact that I am once again all wrapped up in my own flesh.  TMI?  

I like being quiet...When I was a small child I spoke so little it worried my parents.

I have found ways to overcome this part of myself.  Years spent working as a busker in the street and an oil portraitist helped.  It required lots of talking to people.  Yet it was much less about starting conversation than steering them once a conversation had begun.  As a street busker, I learned how to let my presence, tools and signage begin conversations.  I essentially spoke with those people who found me interesting enough to start the conversation themselves.

Cold starting a conversation is frequently hard, especially if I have some agenda other than a simple person to person interaction.  I'm sure this is not unique to me.  Our cities are filled with brave souls attempting to get you talking as they aspire for your signature on a petition, a donation or a chance to tell you why you should support this or that legislation.  These interceptors post themselves right in main pedestrian thoroughfares such as grocery store exits or the end of a crosswalk.  Their choice of posting in itself is off-putting to me.  I'm sure they feel the rejections.  

Unless you've been living on some deserted beach you'll know who I'm writing about.  They are often seen wearing a vest for their cause and/or carrying a clipboard.  When I see these people, I am immediately crossing to the other side of the street or preparing myself for escape with a fixed, determined stare straight into the distance.  I also momentarily go deaf.  It is probable I have accrued some bad interceptor karma. 

In spite of this, I went to Balmy Alley today to be one of these people who wants just a minute of your time.  The alley is famous for its murals.  I waited until about 2:30 in the afternoon.  It was sunny.  The alley was sure to be busy and I was sure to be awake.  I dressed like a regular dude, but carried a small notepad and a pencil.  I had a white t-shirt on with a blue heart on the chest and beige North Face hiking pants.  No vest.  No clipboard.

I won't go into the responses here but I focused on getting the following answered.

1. What do you like about the Alley?

2. If you were ever to commission a mural for yourself, what would it be like?

To my relief, no one I approached refused to speak to me.  Which is interesting, because I think I made it a little hard on myself in that I approached people by simply walking up to them and saying "hi" instead of staking a claim on some specific spot.  Each time I had a distance to cover, and the people I intended to speak with could have turned away as they saw me coming.  Or perhaps it was an unexpected approach and that is what helped it function.

I approached 8 people total, 2 of whom I completely avoided asking my questions. and 6 of whom I found opportunity to get to the point and were willing to talk for some time.  None of whom refused to talk with me.  I found groups of people easier to engage than single people.  I noticed a lot of non committal body language, which took some playfulness and smiles to break down.  

"So, what are you doing here?" is a question which seemed to bring people back.  It is provocative and yet banal at the same time.  It has a weird way of getting people to stay focused on their own journey, whether that be their journey of today or their lifetime.  

It's a question I couldn't help but ask myself as well.