sit in or stake out?

I've seen him quite near twenty-five or thirty times now -- always parked on the same side of the same road -- on my walk to work, and many times on my way back home. 8am, 9am, 12pm, 3pm, 8pm... He sits in an old, light blue Mazda 323LX that sports rugby bumper stickers, and he listens to the radio, reads the Good News, or works on the crossword puzzle in today's news. He is aged, wrinkled and grey, and wears ragged flannel shirts under baggy wool sweaters. I've been meaning to ask him some questions -- if only to settle my own curiosities -- but his open window and my summoned confidence (audacity?) never seem to coincide.