For years I photographed people only from behind or far away. Asking felt intrusive, and I was afraid of hearing no.
This summer I made myself ask one stranger a week. Most said yes. A few said no. Every one of them made me braver.
The asking
The pictures are better when people know you are taking them. They look back, and that look is the photograph.
If you are shy, start with people who are already waiting: at a bus stop, behind a counter, sitting on a bench in the sun.