I met with Rachel later in the evening, we hung out at Bryant Park, and I made use of my defused Speedlight which was held by Rachel's boyfriend at arm's length slightly downward on her from a 45° angle. These days, Bryant Park is a location that works well for me to do street portraits, and at night the park brings exciting lighting options that make intricate patterns and effects that, if used well, could bring interesting results. In addition to street portraits, I also took pictures of Rachel in the ice rink, which served with the opportunity to play with slow shutter speeds and flash and was fun to try.
There's always something new to learn from experimenting with street portraits. Getting nighttime portraits using storefront windows using a lens wide open can only do so much for me. I want my nighttime street portraits to look more natural regardless of where I take them, so the idea of bringing a mid-size octabox with a stand for softer shadows and more separation isn't very appealing to me; that's not the kind of light I see in real life. Sharp shadows make nighttime portraits even more dynamic, and smaller modifiers help me to be more flexible, which is hard to trade-off when I wish to be on the move.