How to achieve street portraiture

Hi there friends! For those of you who personally know me or have seen my previous work, you are use to the fact that I love to get my hand in on capturing portraits. Whether it be of my own babies, other babies, friends who are expecting or family. However, I've made it a goal to venture out and take more portraits but this time, with a purpose. A family friend is graduating high school and my daughter is graduating elementary school. Both are milestones to a child/ teen's