One of the pleasures of film photography is not really knowing how your photos will turn out until the film is developed. You can throw an even bigger wrench into that mysterious mix by shooting with a toy camera, like a Holga or Diana, where your exposure and focus can be all over the place if you're not careful.
Of course, you begin to learn how those toy cameras will respond to certain lighting situations, and how your frame is going to look even when the viewfinder is nowhere near accurate (or at least you'd better hope you learn those quirks before spending so much money on film and processing). I keep notes in a small Moleskine with the focus, framing, lighting, distance and type of film I used to get more consistent photos.
I saw the man above smoking in a small nook between two buildings in Berkeley. The sun was already low and had an orange glow to it when I pulled up in front of him. I knew I wanted to take his photo, but he was sitting in open shade and it was too dark for the film I had in my Holga.
"Hi there! Your outfit and your hair look really cool. Can I take your photo?" I held up my camera to show him it was a plastic toy camera. (I've learned that some people are more likely to say yes to a plastic camera than to a digital one where photos might be posted online immediately.)
"You really think so?" he asked. "Awesome!"
I asked him to come out onto the street and step away from the building just enough to get into the light. After directing him so the light was falling on his face just the way I wanted, I asked him to slowly pull his cigarette up to his mouth and take a drag.
"Thanks!" he said, "I've gotta get back to work."
Off he went and I was dying to know how the photo would turn out. Did he blink? Was his hand obscuring too much of his face? Is the photo going to be way too dark? I had a rough idea, but it's hard to know for sure with a toy camera - especially one with low-speed color reversal film in it (versus color negative, which is more forgiving).
The following week I had the film developed and I was surprised! The photo was as sharp as it could ever be with a cheap plastic lens, the light looked great and the shadows turned out to be an deep, rich blue.
I immediately wished I'd asked him where he worked, or perhaps for his phone number in case he wanted to see the photo.
I remembered the corner where I took the photo in Berkeley, so I called every business nearby until I finally found him.
After finally tracking him down, I sent him a copy after scanning the photo and he messaged me back saying, "Thank you so much! This is so cool! This is the best photo anyone has ever taken of me!"
In the end, the subject was just as surprised with the results as the photographer.