I read To Play the Fool when I want to take a kind of a thrilling vacation.
I've visited San Francisco several times, but have always visited a specific place or event, rather than the city itself. I've been to the Wharf - for about an hour. I've walked up steep hills - 8 1/2 months pregnant and terrified of slipping. I've seen a seal and smelled the fish, and eaten in a seafood restaurant. (I don't eat seafood.)
Reading this book lets me "visit" SF without any of the inconveniences, like trying to drive uphill from a dead stop with a stick-shift car, or trying to find a parking space. (I lost a parked car in SF!)
Fool also gives me an emotional "in" to two communities with which I'm not very familiar - the homeless community and LGBT community. The homeless are always seen as a "problem." This book humanizes the homeless, and helps me talk with them as people rather than as "the homeless."
I'm far more familiar with the gay community, but never really get a chance to experience day-to-day LGBT life. On one hand, they're "just like us" (well, duh!). On the other, they face challenges and inconveniences which I cannot adequately comprehend. Fool helps make the unfamiliar, familiar, and unthreatening.
When you finished To Play the Fool, did you feel as if you'd visited new places and cultures?