Will never forget it. Had already experienced sleeping in my car, which took a bit of getting used to. No car, tried the stay awake all night, sleep on the beach during the day, which might have worked if it wasn't the worst winter rainy season ever. Tried a couple of 'group sleeps' that were less safe than solo sleeps; so exhausted one early AM could not keep eyes open another minute, so curled up in a corner, thinking. "So this is what it's like to sleep on cold concrete. My family (that might have helped & didn't) sleeping in their nice warm beds in their nice warm homes. I can not believe I'm actually sleeping 'downtown' on a sidewalk. How can this be?" My bank nearby, the cybercafe, the main drag I used to drive on. Even the sidewalk I'd walked hundreds of time. Sleeping just behind the wall where Marie sat, homeless, I'd give without her asking, some "share change". "How is it that I'm now sleeping here, on a sidwwalk" is what went through my brain that first night (and many after)
Never slept in the park, a homeless lady recently stabbed to death by other homeless. A place to avoid, for me. Don't like bugs, so even a city sidewalk takes a bit of getting used to. Fear of getting found & in trouble kept me from trying people's backyards, and other 'safe' places.
Shelter's are horrid. Lice and fights and "the shelter hack". Heathier outdoors, and can run when the fighting starts.