I walked by Frank and Scott three times before I stopped and asked to take their photo. The two tattoo artists were joking around outside a tattoo shop, and I had just started shooting street portraits for my 100 Strangers project.

More than 10 years later, I stopped counting but I’m sure I’ve passed 100. There was Mickey who makes a good living impersonating Ben Franklin; Rocky who was part of a 24-hour vigil outside the White House; Molly and Andrew on a first date; and the kid hugging his father’s tombstone in Arlington National Cemetery; and Paper Boy Prince, who just ran for Mayor of New York City.

I started cataloging my street portraits and thought this was a good time to talk about the whole street portrait genre.

If you’ve ever wondered about street portraits, I’ll share what I’ve learned so far. You’ll learn:

• How I decide who to approach;

• How I get them to relax quickly;

• The two questions that get my subjects to open up;

• Who is off limits vs. who is fair game.

Join me March 31 at 7 pm edt for a webinar where we dive into street portraits.